[go: up one dir, main page]

EP1097128A1 - Imidamide derivatives - Google Patents

Imidamide derivatives

Info

Publication number
EP1097128A1
EP1097128A1 EP99936489A EP99936489A EP1097128A1 EP 1097128 A1 EP1097128 A1 EP 1097128A1 EP 99936489 A EP99936489 A EP 99936489A EP 99936489 A EP99936489 A EP 99936489A EP 1097128 A1 EP1097128 A1 EP 1097128A1
Authority
EP
European Patent Office
Prior art keywords
spp
optionally substituted
formula
och
listed
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP99936489A
Other languages
German (de)
French (fr)
Other versions
EP1097128B1 (en
Inventor
Hans-Jochem Riebel
Peter Gerdes
Ernst Rudolf F. Gesing
Achim Hense
Johannes Kanellakopulos
Kristian Kather
Rolf Kirsten
Stefan Lehr
Lothar Rohe
Katharina Voigt
Detlef Wollweber
Wolfram Andersch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE19924273A external-priority patent/DE19924273A1/en
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1097128A1 publication Critical patent/EP1097128A1/en
Application granted granted Critical
Publication of EP1097128B1 publication Critical patent/EP1097128B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C261/00—Derivatives of cyanic acid
    • C07C261/04—Cyanamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/40—Y being a hydrogen or a carbon atom
    • C07C323/41—Y being a hydrogen or an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
    • C07D313/12—[b,e]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/12—Eight-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/28—Halogen atoms

Definitions

  • the present application relates to new imidamide derivatives, a process for their preparation and their use for controlling animal pests.
  • R represents cyano or nitro
  • R 1 represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
  • R 2 represents hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl
  • R 5 where R 4 and R 5 independently of one another represent hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl,
  • R 6 and R 7 independently of one another represent optionally substituted aryl, optionally substituted cycloalkyl or an optionally substituted mono- or bicyclic, nitrogen-free heterocycle,
  • R 8 represents alkyl or optionally substituted aryl
  • Alk stands for alkyl
  • a and A 'independently of one another represent straight-chain or branched alkanediyl and
  • the imidamide derivatives of the formula (I) can also occur as optical and / or geometric isomers, depending on the substituents.
  • the present invention relates both to the various isomer mixtures and to the pure isomers.
  • R - N C - Q - Z
  • R 2 and R 3 have the meaning given above
  • the new imidamide derivatives of the general formula (I) have highly pronounced biological properties and are primarily for combating animal pests, such as insects, arachnids and in particular nematodes, which are used in agriculture, in the forestry, in the protection of stocks and materials occur in the hygiene sector.
  • R preferably represents cyano or nitro.
  • R 1 preferably represents hydrogen, C 1 -C 4 -alkyl which is optionally substituted by halogen, cyano or C ] -C 4 -alkoxy, optionally optionally bis trisubstituted by identical or different manner by halogen or C j -C ⁇ alkyl-substituted C 3 -C 6 cycloalkyl, or represents optionally mono- to trisubstituted by identical or different phenyl, suitable substituents being the phenyl substituents mentioned under R 6 are suitable.
  • R 2 preferably represents hydrogen, C1-C4-alkyl which is optionally substituted by halogen, cyano or C 1 -C alkoxy or is optionally monosubstituted to triple, identically or differently substituted by halogen or CpC ⁇ alkyl, C 3 -C 6 -cycloalkyl.
  • R 3 preferably represents the groups —C— XR. - YR and _Q - p
  • R 4 and R 5 are each independently preferably hydrogen, where appropriate, by halogen, cyano or C j -C 4 alkoxy
  • C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl which are optionally monosubstituted to trisubstituted, identically or differently, by halogen or C1-C 4 -alkyl.
  • R 6 and R 7 independently of one another, preferably each represent phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl which are optionally mono- to pentasubstituted or substituted differently, where the following may be mentioned as substituents: hydroxy, amino, cyano, nitro, halogen; in each case optionally substituted by hydroxy, cyano or pialogenes C 1 -C 4 alkyl, Ci -
  • Bromine optionally substituted C 2 -C 6 cycloalkyl and optionally phenyl; further C 1 -C 4 alkyl, C r C 4 alkoxy and C r C 4 - haloalkyl and C 1 -C 4 haloalkoxy each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; and for an optionally mono- to pentasubstituted, identically or differently substituted, saturated or partially unsaturated or unsaturated mono- or tricyclic nitrogen-free heterocycle having 4 to 10 carbon atoms and 1 to 3 identical or different heteroatoms, such as O and S atoms, the substituents being those at
  • X preferably represents C 1 -C 4 -alkyl or each mono- to pentasubstituted, identically or differently substituted, phenyl and naphthyl, the phenyl substituents mentioned for R 6 being suitable as substituents.
  • X preferably represents a single bond, each straight-chain or branched Cj-Cg-alkanediyl, C 2 -C6 -alkenediyl or C 2 -C, 5-alkynediyl and for the groups -AO-, -AS-, -AO-A ' -, -AS-A'-, -AN (Alk) - or -AN (Alk) -A'-, where
  • Alk preferably represents C 1 -C 4 -alkyl
  • a and A 'independently of one another are preferably straight-chain or branched Cj-C 6 -alkanediyl.
  • Y preferably represents a single bond
  • R particularly preferably represents cyano or nitro.
  • R 1 particularly preferably represents hydrogen, in each case optionally by
  • Phenyl where the phenyl substituents mentioned for R 6 are suitable as substituents.
  • R 2 particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or in each case optionally Single to triple, the same or different, fluorine, chlorine, bromine, methyl or ethyl substituted cyclopropyl, cyclopentyl and cyclohexyl.
  • R 3 particularly preferably represents the groupings and _ 0 - R 8 , in which
  • R 4 and R 5 independently of one another are particularly preferably hydrogen, for methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl which are each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for cyclopropyl, cyclopentyl and cyclohexyl which are optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl or ethyl.
  • R 6 and R 7 independently of one another are particularly preferably each phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl which may be monosubstituted to trisubstituted by identical or different substituents, the following being mentioned as substituents: cyano, nitro, amino, fluorine, chlorine, bromine; each optionally substituted by fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino or dimethylamino; in each case optionally substituted by fluorine and / or chlorine, acetyl, propionyl, methoxycarbonyl,
  • Cyano nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio and dimethylamino.
  • R 8 is particularly preferably methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl or phenyl which is optionally monosubstituted to trisubstituted identically or differently, the phenyl substituents mentioned for R 6 being suitable as substituents.
  • X particularly preferably stands for a single bond and for
  • Y particularly preferably stands for a single bond and for
  • R very particularly preferably represents cyano or nitro.
  • R 1 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, cyclopropyl or phenyl.
  • R 2 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl or cyclopropyl.
  • R 3 very particularly preferably represents the groupings
  • R 4 and R 5 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, n- or i-propyl and cyclopropyl.
  • R 6 and R 7 independently of one another very particularly preferably represent phenyl or naphthyl which may be monosubstituted to trisubstituted identically or differently, the following being mentioned as substituents:
  • Cyano nitro, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, difluoromethyl , Trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methylamino, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl,
  • Methylsulfonyl methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl and diethylaminocarbonyl; and in each case optionally by cyano, nitro, fluorine, chlorine, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl or trifluoromethoxy, trifluoromethylthio,
  • substituents may be mentioned: cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, trifluoromethyl or dimethylamino or optionally substituted phenyl, the substituents being suitable for the phenyl radical come, which are also mentioned under R 6 for the phenyl radical.
  • R 8 very particularly preferably for methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl or phenyl which is optionally monosubstituted to trisubstituted identically or differently, the phenyl substituents mentioned for R 6 being suitable as substituents.
  • X very particularly preferably stands for a single bond and for
  • Preferred compounds according to the invention are substances of the formulas (I a) to (I h):
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , X and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
  • Preferred compounds according to the invention are also substances of the formulas (I A) to
  • NC - N C-NH-R 3
  • R 3 , R 4 , R 5 and R 6 represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
  • Preferred compounds according to the invention are also substances of the formulas (I-I) to (1-56)
  • NC - N C ⁇ NI - CH ⁇ 2 -R ° i 1 - ,. (1-3)
  • NC - N C - N - CH (CH,) - CH ⁇ -R 6
  • NC - N C - N - CH (CH 3 ) - CH 2 CH - R 6
  • NC - N C - N - OCH (CH 3 ) CH 2 CH - R 7 1 1 o (1-14)
  • NC - N C - N - CHj. - (CH 2,) 'Z -R b (1-15)
  • NC - N C - N - CH (CH 3 ) - (CH 2 ) - R 6
  • NC— N C— N-OCH (CH 3 ) CH 2 O— R 7 1 (1-20)
  • NC - N CI - NI - CH 2 - CH, 2S - R D
  • NC - N C - NO (CH 2 ) 2 SO-R 7
  • NC - N C - NO (CH 2 ) 2 SO 2 -R 7
  • NC - N C - N - CH (CH 3 ) - CH 2 OCH - R 6
  • NC - N C - N - CH (CH - CH, SCH - R 6
  • NC— N C— N-CH (CH,) - CH, SOCH R 6 1 '9 (1-38)
  • NC - N C - N - CH (CH 3 ) - CH 2 CH 2 S - R 6
  • NC— N C— N-CH -CH 2 N (CH 3 ) - R b (1-49)
  • NC - N C - N - CHr - N (C, H - R 6
  • NC - N C - N - CH 2 - CH 2 CH 2 N (CH 3 ) -R 6
  • NC - N C - N - CH - CH 2 N (C 2 H 5 ) CH R 6
  • NC— N C— N-CH— CH 2 CH 2 N (CH 3 ) CH R 6 1 I 9 (1-55)
  • R 1 , R 2 , R 6 and R 7 stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
  • hydrocarbon radicals such as alkyl or alkenyl - also in connection with heteroatoms, such as alkoxy or alkyl thio - are in each case straight-chain or branched as far as possible.
  • R 1 , R 2 and XR 6 as listed in Table 1.
  • R 1 , R 2 and XR 6 as listed in Table 1.
  • R 1 , R 2 and XR 6 as listed in Table 1.
  • R 1 , R 2 and XR 6 as listed in Table 1.
  • R i C 3 H 7 -i
  • R 2 C 2 H 5
  • R 2 C 2H 5
  • R 2 C 3 H 7 -i
  • R 2 C 2 H 5
  • R 2 C 2 H 5
  • R l C 3 H 7 -n
  • R 2 C 2 H 5
  • R 2 C 2 H 5
  • R i C 2 H 5
  • R 2 H YR 7 as listed in Table 1 15. 00/03976 - 34 -
  • Table 120 Compounds in Table 120 correspond to the general formula (I c), in which
  • YR 7 as listed in Table 1 15 on A. 00/03976 _ 35 _
  • Table 125 Compounds in Table 125 correspond to the general formula (I c), in which
  • R 2 C 2 H 5
  • R 2 C 3 H 7 -i
  • Table 130 Compounds in Table 130 correspond to the general formula (I c), in which
  • R 2 C 2 H 5
  • R6 vvie listed in table b, as well as additional
  • R 6 as listed in Table e.
  • NC— N CN— Y - R 7 L.1 'n (I c)
  • Formula (II) provides a general definition of the ethanimide esters required as starting materials for carrying out the process according to the invention.
  • Z is preferably C 4 -C 4 -alkyl, in particular methyl or ethyl.
  • N-cyanoethanimidic acid esters are largely known (see, for example, US 5,304,566 or J. Org. Chem. 28, 1963, 1816-1821) and / or can be obtained by customary processes.
  • N-nitro-ethanimidic acid esters are obtained, for example, by nitrating the corresponding NO 2 -free ethanimidic acid esters of the formula (II) in a conventional manner.
  • the amines of the general formula (III) to be used as starting materials in the process according to the invention are generally known compounds of organic chemistry or can be obtained in a generally known manner.
  • the process according to the invention is preferably carried out in the presence of a diluent.
  • Alcohols such as methanol and ethanol can preferably be used; Nitriles such as acetonitrile or esters such as ethyl acetate. It is also possible to work in water or organic-aqueous mixtures if necessary.
  • reaction temperatures can be carried out when carrying out the process according to the invention.
  • Process can be varied over a wide range. In general, temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 80 ° C.
  • the end products are worked up and isolated in a generally known manner.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
  • Chilopoda for example, Geophilus carpophagus and Scutigera spp.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci
  • Aleurodes brassicae Bemisia tabaci
  • Trialeurodes vaporariorum Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigususpp.
  • Leptinotarsa decemlineata Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatordimidhmpphppm, spp.
  • Anthrenus spp. Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha., Amphimalltra solitus
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp.
  • Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Flyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomy
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,
  • Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursa.
  • the compounds of the formula (I) according to the invention are notable in particular for good nematicidal activity. For example, they can be used with particularly good success to combat Meloidogyne incognita
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.
  • the compounds according to the invention show herbicidal effects in some cases.
  • These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar
  • Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Talc chalk, quartz, attapulgite, montmorillonite or diatomaceous earth ' and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g.
  • suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compound according to the invention can be mixed with other active compounds, such as insecticides, attractants, sterilants, bactericides,
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Fungicides are particularly favorable mixed partners:
  • Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flutilanol, Flusil- fililol, Flusilanol, Flusil- fililol, Flusil- fililol, Flusil- fililol-, Flusil- fidol, Flusil- fidol, Flusil- fidil, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flus
  • copper preparations such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and Bordeaux mixture,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin.
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemo ⁇ h, triflumizole, triforine, triticonazole, O 00/03976
  • Bacillus thuringiensis Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,
  • Fipronil fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
  • HCH heptenophos, hexaflumuron, hexythiazox, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
  • Methamidophos Methidathion, Methiocarb, Methomyl, Metolcarb, Mübemectin, Monocrotophos, Moxidectin,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
  • Tebufenozid Tebufenpyrad
  • Tebupirimiphos Teflubenzuron
  • Tefluthrin Temephos
  • .Terbam Terbufos
  • Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuringiensin, Tralomenhriazonium, Tralomenhriazon, Tronomenhrononium, Tronomenhrononium, Tronomenhriazon
  • the active compounds according to the invention can also be used in their commercially available formulations and in the formulations thereof
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • the compounds according to the invention also show herbicidal properties or plant growth-regulating activity, such as a defoliant effect.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae and lice. Hair lice, featherlings and fleas.
  • animal parasites ectoparasites
  • ectoparasites such as tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae and lice. Hair lice, featherlings and fleas.
  • parasites include: From the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .. From the order Diptera and the subordinates Nematocerina and Brachycerina e.g.
  • Hybomitra spp. Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp ., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp.
  • Tyrophagus spp. Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats,
  • Infest hamsters, guinea pigs, rats and mice By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets,
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Kalotermes flavicollis such as Lepisma saccarina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
  • Agents or mixtures containing them can be protected is to be understood as examples: construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry work or wooden products, which are generally used in house construction or in carpentry.
  • the active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and, if appropriate, dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, Te ⁇ entinöl and Like. Used.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochlomaphthalene, preferably ⁇ -monochloronaphthalene, are used. O 00/03976
  • organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are the water-thinnable and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin.
  • binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as in
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, in itself Known dyes, pigments, water-repellent agents, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixative (mixture) or a Weichrnacher (mixture). These additives are intended to volatilize the active ingredients and crystallize or precipitate! prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • the insecticides and fungicides mentioned in Wo 94/29 268 are particularly suitable as additional mixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Very particularly preferred mixing partners can be insecticides, such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin,
  • Permethrin Permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlofluanid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl -isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlofluanid, tolylfluanid, 3-io
  • Test nematode Meloidogyne incognita
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is mixed intimately with the soil that is contaminated with the test nematodes.
  • the treated soil is poured into pots, seeds are sown and the pots are kept at a greenhouse temperature of 25 ° C.
  • the lettuce roots are examined for nematode infestation (root galls) and the efficiency of the active ingredient is determined in%.
  • the efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is as high as that of the control plants in untreated, but equally contaminated soil.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

The invention relates to novel imidamide derivatives of formula (I), wherein R, R?1, R2 and R3¿ have the meaning mentioned in the description. The invention also relates to a method of production and to the use of said derivatives for combating animal pests such as insects, arachnids and especially nematodes.

Description

Imidamid-DerivateImidamide derivatives
Die vorliegende Anmeldung betrifft neue Imidamid-Derivate, ein Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von tierischen Schädlingen.The present application relates to new imidamide derivatives, a process for their preparation and their use for controlling animal pests.
Bestimmte Imidamid-Derivate sind bereits bekannt (vgl. WO 91 04 965, WO 93 04 032, EP 0 403 159; J. Organomet. Chem. (1975), 97 (1), S. 39 - 44; Bull. Soc. Chim. Belg. (1981), 90 (1), S 89 - 98). Auch insektizide Eigenschaften einiger dieser Verbindungen waren bekannt.Certain imidamide derivatives are already known (cf. WO 91 04 965, WO 93 04 032, EP 0 403 159; J. Organomet. Chem. (1975), 97 (1), pp. 39-44; Bull. Soc. Chim. Belg. (1981), 90 (1), pp 89-98). Insecticidal properties of some of these compounds were also known.
Es wurden nun neue Imidamid-Derivate der allgemeinen Formel (I) gefunden,New imidamide derivatives of the general formula (I) have now been found
in welcher in which
R für Cyano oder Nitro steht,R represents cyano or nitro,
R1 für Wasserstoff, gegebenenfalls substituiertes Alkyl, gegebenenfalls substi- tuiertes Cycloalkyl oder gegebenenfalls substituiertes Phenyl steht,R 1 represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
R2 für Wasserstoff, gegebenenfalls substituiertes Alkyl oder gegebenenfalls substituiertes Cycloalkyl steht undR 2 represents hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl and
R4 R3 für die Gruppierungen — C-X-R6 • ~Y"R7 und -O-R8 steh*, R 4 R3 for the groupings - CXR 6 • ~ Y "R 7 and -OR 8 stand * ,
R5 wobei R4 und R5 unabhängig voneinander für Wasserstoff, gegebenenfalls substituiertes Alkyl oder gegebenenfalls substituiertes Cycloalkyl stehen,R 5 where R 4 and R 5 independently of one another represent hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl,
R6 und R7 unabhängig voneinander für gegebenenfalls substituiertes Aryl, gegebenenfalls substituiertes Cycloalkyl oder für einen gegebenenfalls substituierten mono- oder bicyclischen, Stickstoff-freien Heterocyclus stehen,R 6 and R 7 independently of one another represent optionally substituted aryl, optionally substituted cycloalkyl or an optionally substituted mono- or bicyclic, nitrogen-free heterocycle,
R8 für Alkyl oder gegebenenfalls substituiertes Aryl steht,R 8 represents alkyl or optionally substituted aryl,
X für eine Einfachbindung, für jeweils geradkettiges oder verzweigtesX for a single bond, for each straight-chain or branched
Alkandiyl, Alkendiyl, Alkindiyl sowie für die Gruppierungen -A-O-, -A-S-, -A-O-A'-, -A-S-A'-, -A-N(Alk)- oder -A-N(Alk)-A'- steht, wobei der Teil A an das C-Atom der Gruppierung -C(R4R5)-X-R6 ge- bunden ist;Alkanediyl, alkenediyl, alkindiyl and for the groups -AO-, -AS-, -AO-A'-, -AS-A'-, -AN (Alk) - or -AN (Alk) -A'-, where part A is bound to the C atom of the group -C (R 4 R 5 ) -XR 6 ;
Alk für Alkyl steht undAlk stands for alkyl and
A und A' unabhängig voneinander für geradkettiges oder ver- zweigtes Alkandiyl stehen undA and A 'independently of one another represent straight-chain or branched alkanediyl and
Y für eine Einfachbindung sowie die Gruppierungen -O-A-, -O-A"-O-,Y for a single bond and the groupings -O-A-, -O-A "-O-,
-O-A"-S-, -O-A"-SO-, -O-A"-SO2-, -O-A"-O-A'- oder -O-A"-S-A'- steht, wobei das O-Atom dieser Gruppierung immer an dem N-Atom des Grundgerüsts der Formel (I) verknüpft ist;-OA "-S-, -OA" -SO-, -OA "-SO 2 -, -OA"-O-A'- or -OA "-S-A'-, where the O atom of this grouping is always linked to the N atom of the basic structure of the formula (I);
A und A' die oben angegebene Bedeutung haben undA and A 'have the meaning given above and
A" für geradkettiges oder verzweigtes Alkandiyl mit mindestens 2 Kohlenstoffatomen zwischen den Heteroatomen steht. it der Maßgabe, daß für R = CN und R2 = H die Verbindungen, in welcherA "stands for straight-chain or branched alkanediyl having at least 2 carbon atoms between the heteroatoms. with the proviso that for R = CN and R 2 = H the compounds in which
R = n-C4H9 und R3 = _CH ~ bzw.R = nC 4 H 9 and R 3 = _CH ~ or
Ri = CH3 und R3 = bzw. Ri = CH 3 and R3 = respectively .
Ri = C2H5 und R3 = —/ bzw.R i = C 2 H 5 and R 3 = - / or
R1 = CH3 und R3 = — ~ bzw.R 1 = CH 3 and R 3 = - ~ or
ausgenommen sind.with exception of.
Die Imidamid-Derivate der Formel (I) können, auch in Abhängigkeit von den Substituenten, als optische und/oder geometrische Isomere vorkommen. Die vorliegende Erfindung betrifft sowohl die verschiedenen Isomerengemische als auch die reinen Isomeren.The imidamide derivatives of the formula (I) can also occur as optical and / or geometric isomers, depending on the substituents. The present invention relates both to the various isomer mixtures and to the pure isomers.
Man erhält die neuen Imidamid-Derivate der allgemeinen Formel (I), wenn man Ethanimidsäureester der Formel (II)The new imidamide derivatives of the general formula (I) are obtained if ethanimidates of the formula (II)
R— N=C — Q— ZR - N = C - Q - Z
1 , (II) 1 , (II)
R in welcher R und R1 die oben angegebene Bedeutung haben,R in which R and R 1 have the meaning given above,
Q für Sauerstoff oder Schwefel steht undQ stands for oxygen or sulfur and
Z für Alkyl steht,Z represents alkyl,
mit Aminen der Formel (III)with amines of the formula (III)
H-N — RJ III) R l 2 ( 2 in welcherHN - R J III) R l 2 ( 2 in which
R2 und R3 die oben angegebene Bedeutung habenR 2 and R 3 have the meaning given above
in Gegenwart eines Verdünnungsmittels umsetzt.in the presence of a diluent.
Die neuen Imidamid-Derivate der allgemeinen Formel (I) besitzen stark ausgeprägte biologische Eigenschaften und sind vor allem zur Bekämpfung von tierischen Schädlingen, wie Insekten, Spinnentieren und insbesondere Nematoden, die in der Landwirtschaft, in den Forsten, im Vorrats- und Materialschutz sowie auf dem Hygiene- sektor vorkommen, geeignet.The new imidamide derivatives of the general formula (I) have highly pronounced biological properties and are primarily for combating animal pests, such as insects, arachnids and in particular nematodes, which are used in agriculture, in the forestry, in the protection of stocks and materials occur in the hygiene sector.
Die erfindungsgemäßen Verbindungen sind durch die Formel (I) allgemein definiert. Bevorzugte Substituenten bzw. Bereiche der in den oben und nachstehend erwähnten Formeln aufgeführten Reste werden im folgenden erläutert.The compounds according to the invention are generally defined by the formula (I). Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below.
R steht bevorzugt für Cyano oder Nitro.R preferably represents cyano or nitro.
R1 steht bevorzugt für Wasserstoff, für gegebenenfalls durch Halogen, Cyano oder C]-C4-Alkoxy substituiertes C C^-Alkyl, für gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Halogen oder Cj-C^Alkyl substituiertes C3-C6-Cycloalkyl oder für gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, wobei als Substituenten die bei R6 genannten Phenylsubstituenten infrage kommen.R 1 preferably represents hydrogen, C 1 -C 4 -alkyl which is optionally substituted by halogen, cyano or C ] -C 4 -alkoxy, optionally optionally bis trisubstituted by identical or different manner by halogen or C j -C ^ alkyl-substituted C 3 -C 6 cycloalkyl, or represents optionally mono- to trisubstituted by identical or different phenyl, suitable substituents being the phenyl substituents mentioned under R 6 are suitable.
R2 steht bevorzugt für Wasserstoff, für gegebenenfalls durch Halogen, Cyano oder Cι-C -Alkoxy substituiertes C1-C4- Alkyl oder für gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Halogen oder CpC^Alkyl substituiertes C3-C6-Cycloalkyl.R 2 preferably represents hydrogen, C1-C4-alkyl which is optionally substituted by halogen, cyano or C 1 -C alkoxy or is optionally monosubstituted to triple, identically or differently substituted by halogen or CpC ^ alkyl, C 3 -C 6 -cycloalkyl.
R4 R 4
R3 steht bevorzugt für die Gruppierungen -C— X-R . — Y-R und _Q — pR 3 preferably represents the groups —C— XR. - YR and _Q - p
R5 wobeiR 5 where
R4 und R5 unabhängig voneinander bevorzugt für Wasserstoff, für gege- benenfalls durch Halogen, Cyano oder Cj-C4-Alkoxy substituiertesR 4 and R 5 are each independently preferably hydrogen, where appropriate, by halogen, cyano or C j -C 4 alkoxy
C1-C4- Alkyl oder für gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Halogen oder C1-C4- Alkyl substituiertes C3-C6- Cycloalkyl stehen.C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl which are optionally monosubstituted to trisubstituted, identically or differently, by halogen or C1-C 4 -alkyl.
R6 und R7 unabhängig voneinander bevorzugt für jeweils gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes Phenyl, Naphthyl, Dihydronaphthyl und Tetrahydronaphthyl stehen, wobei als Substituenten genannt seien: Hydroxy, Amino, Cyano, Nitro, Halogen; jeweils gegebenenfalls durch Hydroxy, Cyano oder Pialogen substituiertes C1-C4- Alkyl, Ci -R 6 and R 7, independently of one another, preferably each represent phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl which are optionally mono- to pentasubstituted or substituted differently, where the following may be mentioned as substituents: hydroxy, amino, cyano, nitro, halogen; in each case optionally substituted by hydroxy, cyano or pialogenes C 1 -C 4 alkyl, Ci -
C4-Alkoxy, Cι -C4-Alkylamino und Di-(C]-C4-)Alkylamino; jeweils gegebenenfalls durch Halogen substituiertes Cι-C4-Alkyl-carbonyl, C ] -C4-Alkoxy-carbonyl, C 1 -C4-Alkyl-carbonyl-amino, C 1 -C4-Alkyl- thio, C C^-Alkylsulfinyl und C]-C -Alkylsulfonyl; Aminocarbonyl, Aminothiocarbonyl, Cι-C4-Alkylaminocarbonyl, Di-(C;, -C4)-alkyι- amino-carbonyl, Aminosulfonyl, C1-C4-Alkylaminosulfonyl und Di- (Cι-C4)-alkylamino-sulfonyl; sowie jeweils gegebenenfalls durch Hydroxy, Cyano, Nitro, Halogen, Cι-C4-Alkyl, Cι-C4-Alkoxy, Cj- C4-Alkylthio, CrC4-Alkylsulfιnyl, CrC4-Alkylsulfonyl und CrC4-C 4 alkoxy, -C -C 4 alkylamino and di- (C ] -C 4 -) alkylamino; each optionally substituted by halogen -CC 4 alkyl carbonyl, C ] -C 4 alkoxy carbonyl, C 1 -C 4 alkyl carbonylamino, C 1 -C 4 alkyl thio, CC ^ alkyl sulfinyl and C ] -C alkyl sulfonyl; Aminocarbonyl, Aminothiocarbonyl, C 1 -C 4 -alkylaminocarbonyl, di- (C 1 -C 4 ) -alkyl-amino-carbonyl, aminosulfonyl, C 1 -C 4 -alkylaminosulfonyl and di- (-C-C4) -alkylaminosulfonyl; and in each case optionally substituted by hydroxyl, cyano, nitro, halogen, Cι-C 4 -alkyl, C 4 alkoxy, C j - C 4 alkylthio, C r C 4 -Alkylsulfιnyl, C r C 4 alkylsulfonyl and C r C 4 -
Halogenalkyl, C]-C4-Halogenalkoxy, CrC4-Halogenalkylthio, Ci- C -Halogenalkylsulfιnyl und Cj-C4-Halogenalkylsulfonyl mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom substituiertes Phenyl, Phenoxy, Phenylthio, Phenylsulfinyl, Phenylsulfonyl, Benzyl und Phenylamino; weiterhin für jeweils gegebenenfalls einfach bis fünffach, gleich oder verschieden substituiertes C3-C12-Cycloalkyl oder C5-Cn-Cyclo- alkenyl stehen, wobei als Substituenten genannt seien: Halogen, gegebenenfalls substituiertes C,-C4-Alkyl, wobei als Substituenten bevorzugt genannt seien: Halogen, wie Fluor, Chlor,Haloalkyl, C] -C 4 -haloalkoxy, C r C 4 -haloalkylthio, Ci- C -haloalkylsulfionyl and C j -C 4 -haloalkylsulfonyl, each with 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine substituted phenyl, Phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzyl and phenylamino; furthermore represent in each case monosubstituted to pentasubstituted, identically or differently substituted C 3 -C 12 -cycloalkyl or C 5 -C n -cycloalkenyl, the following being mentioned as substituents: halogen, optionally substituted C 1 -C 4 -alkyl, where the following may be mentioned as preferred substituents: halogen, such as fluorine, chlorine,
Brom, gegebenenfalls substituiertes C2-C6-Cycloalkyl und gegebenenfalls Phenyl; ferner Cι-C4-Alkyl, CrC4-Alkoxy sowie CrC4- Halogenalkyl und Cι-C4-Halogenalkoxy mit jeweils 1 bis 5 gleichen oder verschiedenen Halogenatomen aus der Reihe Fluor, Chlor und Brom; sowie für einen gegebenenfalls einfach bis fünffach, gleich oder verschieden substituierten, gesättigten bzw. teilweise ungesättigten bzw. ungesättigten mono- bi- oder tricyclischen Stickstoff-freien Hetero- cyclus mit 4 bis 10 C- Atomen und 1 bis 3 gleichen oder verschiedenen Heteroatomen, wie O- und S-Atome, wobei als Substituenten die beiBromine, optionally substituted C 2 -C 6 cycloalkyl and optionally phenyl; further C 1 -C 4 alkyl, C r C 4 alkoxy and C r C 4 - haloalkyl and C 1 -C 4 haloalkoxy each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine; and for an optionally mono- to pentasubstituted, identically or differently substituted, saturated or partially unsaturated or unsaturated mono- or tricyclic nitrogen-free heterocycle having 4 to 10 carbon atoms and 1 to 3 identical or different heteroatoms, such as O and S atoms, the substituents being those at
R6 genannten Phenylsubstituenten infrage kommen.R 6 mentioned phenyl substituents come into question.
steht bevorzugt für Cι-C4-Alkyl oder für jeweils einfach bis fünffach, gleich oder verschieden substituiertes Phenyl und Naphthyl, wobei als Substituenten die bei R6 genannten Phenylsubstituenten infrage kommen. X steht bevorzugt für eine Einfachbindung, für jeweils geradkettiges oder verzweigtes Cj-Cg- Alkandiyl, C2-C6-Alkendiyl oder C2-C,5- Alkindiyl sowie für die Gruppierungen -A-O-, -A-S-, -A-O-A'-, -A-S-A'-, -A-N(Alk)- oder -A-N(Alk)-A'-, wobeipreferably represents C 1 -C 4 -alkyl or each mono- to pentasubstituted, identically or differently substituted, phenyl and naphthyl, the phenyl substituents mentioned for R 6 being suitable as substituents. X preferably represents a single bond, each straight-chain or branched Cj-Cg-alkanediyl, C 2 -C6 -alkenediyl or C 2 -C, 5-alkynediyl and for the groups -AO-, -AS-, -AO-A ' -, -AS-A'-, -AN (Alk) - or -AN (Alk) -A'-, where
Alk bevorzugt für Cj-C4-Alkyl steht undAlk preferably represents C 1 -C 4 -alkyl and
A und A' unabhängig voneinander bevorzugt für geradkettiges oder verzweigtes Cj-C6-Alkandiyl stehen.A and A 'independently of one another are preferably straight-chain or branched Cj-C 6 -alkanediyl.
Y steht bevorzugt für eine Einfachbindung sowie dieY preferably represents a single bond and the
Gruppierungen -O-A-, -O-A"-O-, -O-A"-S-, -O-A"-SO-, -O-A"-SO2-, -O-A"-O-A'- oder -O-A"-S-A'-, wobeiGroupings -OA-, -OA "-O-, -OA" -S-, -OA "-SO-, -OA" -SO 2 -, -OA "-O-A'- or -OA" -S- A'-, where
A und A' die oben angegebene bevorzugte Bedeutung haben.A and A 'have the preferred meaning given above.
A" bevorzugt für geradkettiges oder verzweigtes (C2-C4)- Alkandiyl mit mindestens 2 Kohlenstoffatomen zwischen denA "preferred for straight-chain or branched (C 2 -C 4 ) alkanediyl with at least 2 carbon atoms between the
Heteroatomen steht.Heteroatoms stands.
vorzugten Definitionen beinhalten die Maßgabe, daß für R = CN und R2 = H rbindungen, in welchenPreferred definitions contain the proviso that for R = CN and R 2 = H bonds, in which
R1 = CH, und R3 = bzw. R 1 = CH, and R 3 = or
Ri = C2H5 und R3 = —f~ bzw.R i = C 2 H 5 and R 3 = —f ~ or
Ri = CH3 und R3 = _ f~\ bzw.R i = CH 3 and R 3 = _ f ~ \ or
Ri = i-C3H7 und R3 = _^~ _CH3 R i = iC 3 H 7 and R 3 = _ ^ ~ _ CH3
ausgenommen sind.with exception of.
R steht besonders bevorzugt für Cyano oder Nitro.R particularly preferably represents cyano or nitro.
R1 steht besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durchR 1 particularly preferably represents hydrogen, in each case optionally by
Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl und n-, i-, s- oder t-Butyl; für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Methyl oder Ethyl substituiertes Cyclopropyl, Cyclopentyl und Cyclohexyl oder für ge- gebenenfalls einfach bis dreifach, gleich oder verschieden substituiertesCyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl; for cyclopropyl, cyclopentyl and cyclohexyl which are optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl or ethyl or for optionally monosubstituted to trisubstituted, identically or differently
Phenyl, wobei als Substituenten die bei R6 genannten Phenylsubstituenten infrage kommen.Phenyl, where the phenyl substituents mentioned for R 6 are suitable as substituents.
R2 steht besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl und n-, i-, s- oder t-Butyl, oder für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Methyl oder Ethyl substituiertes Cyclopropyl, Cyclopentyl und Cyclohexyl.R 2 particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or in each case optionally Single to triple, the same or different, fluorine, chlorine, bromine, methyl or ethyl substituted cyclopropyl, cyclopentyl and cyclohexyl.
R3 steht besonders bevorzugt für die Gruppierungen und _0— R8, wobeiR 3 particularly preferably represents the groupings and _ 0 - R 8 , in which
R4 und R5 unabhängig voneinander besonders bevorzugt für Wasserstoff, für jeweils gegebenenfalls durch Cyano, Fluor, Chlor, Methoxy oder Ethoxy substituiertes Methyl, Ethyl, n- oder i-Propyl und n-, i-, s- oder t-Butyl, oder für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Brom, Methyl oder Ethyl substituiertes Cyclopropyl, Cyclopentyl und Cyclohexyl stehen.R 4 and R 5 independently of one another are particularly preferably hydrogen, for methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl which are each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for cyclopropyl, cyclopentyl and cyclohexyl which are optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl or ethyl.
R6 und R7 unabhängig voneinander besonders bevorzugt für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl, Naphthyl, Dihydronaphthyl und Tetrahydronaphthyl stehen, wobei als Substituenten genannt seien: Cyano, Nitro, Amino, Fluor, Chlor, Brom; jeweils gegebenenfalls durch Fluor oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, n-, i-, s- oder t-Butoxy, Methylamino, Ethylamino, n- oder i-Propylamino oder Dimethylamino; jeweils gegebenenfalls durch Fluor und/oder Chlor substituiertes Acetyl, Propionyl, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Methylsulfinyl, Methylsul- fonyl, Ethylthio, Ethylsulfinyl oder Ethylsulfonyl; Aminocarbonyl, Aminothiocarbonyl, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylaminocarbonyl, Diethylamino- carbonyl, Aminosulfonyl, Methylaminosulfonyl, Ethylaminosulfonyl,R 6 and R 7 independently of one another are particularly preferably each phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl which may be monosubstituted to trisubstituted by identical or different substituents, the following being mentioned as substituents: cyano, nitro, amino, fluorine, chlorine, bromine; each optionally substituted by fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino or dimethylamino; in each case optionally substituted by fluorine and / or chlorine, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl or ethylsulfonyl; Aminocarbonyl, aminothiocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, aminosulfonyl, methylaminosulfonyl, ethylaminosulfonyl,
Dimethylaminosulfonyl und Diethylaminosulfonyl; sowie jeweils gegebenenfalls durch Cyano, Nitro, Fluor, Chlor, Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Trifluormethyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, n- oder i-Propylsulfmyl, Methyl- sulfonyl, Ethylsulfonyl, n- oder i-Propylsulfonyl, Difluormethoxy oder Trifluormethoxy, Tπfluormethylthio, Trifluormethylsulfinyl oder Trifluormethylsulfonyl substituiertes Phenyl, Phenoxy, Phenylthio, Phenylsulfinyl, Phenylsulfonyl, Benzyl oder Phenylamino; ferner für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, n- oder i-Propyl, gegebenenfalls substituiertes Cyclohexyl-C,-C4-alkyl, gegebenenfalls substituiertes Phenyl-C,-C4-alkyl, Methoxy, Ethoxy, Trifluormethyl oder Trifluormethoxy substituiertes Cyclopentan, Cyclohexan, Cyclo- penten und Cyclohexen stehen; sowie für einen gegebenenfalls einfach bis fünffach, gleich oder verschieden substituierten, gesättigten bzw. teilweise ungesättigten bzw. ungesättigten mono- oder bicyclischen Stickstoff-freien Heterocyclus mit 4 bis 9 C- Atomen und 1 bis3 gleichen oder verschiedenen Hetero- atomen, wie O- und S-Atome, stehen, wobei als Substituenten genannt seien:Dimethylaminosulfonyl and diethylaminosulfonyl; and in each case optionally by cyano, nitro, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, methylthio , Ethylthio, n- or i-propylthio, Methylsulfinyl, ethylsulfinyl, n- or i-Propylsulfmyl, methyl sulfonyl, ethylsulfonyl, n- or i-propylsulphonyl, difluoromethoxy or trifluoromethoxy, Tπfluormethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl-substituted phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzyl or phenylamino; furthermore for each optionally single to triple, identical or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl, optionally substituted cyclohexyl-C, -C 4 -alkyl, optionally substituted phenyl-C, -C 4 -alkyl , Methoxy, ethoxy, trifluoromethyl or trifluoromethoxy substituted cyclopentane, cyclohexane, cyclopentene and cyclohexene; and for an optionally mono- to pentasubstituted, identically or differently substituted, saturated or partially unsaturated or unsaturated mono- or bicyclic nitrogen-free heterocycle having 4 to 9 C atoms and 1 to 3 identical or different hetero atoms, such as O and S atoms, where the following may be mentioned as substituents:
Cyano, Nitro, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Ethoxy, Trifluormethyl, Trifluormethoxy, Trifluormethyl- thio und Dimethylamino.Cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio and dimethylamino.
R8 besonders bevorzugt für Methyl, Ethyl, n- oder i-Propyl; n-, i-, s- oder t-Butyl oder für gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl steht, wobei als Substituenten die bei R6 genannten Phenylsubstituenten infrage kommen.R 8 is particularly preferably methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl or phenyl which is optionally monosubstituted to trisubstituted identically or differently, the phenyl substituents mentioned for R 6 being suitable as substituents.
X steht besonders bevorzugt für eine Einfachbindung sowie für dieX particularly preferably stands for a single bond and for
Gruppierungen:Groupings:
-CH2-, -(CH2)2-, -(CH2)3-, -(CH2)4-, -CH(CH3)-, -CH(C2H5)-, -CH(CH3)CH2-, -CH2CH(CH3)-, -CH(CH3)CH2CH2-, -C(CH3)2-,-CH 2 -, - (CH 2 ) 2 -, - (CH 2 ) 3 -, - (CH 2 ) 4 -, -CH (CH 3 ) -, -CH (C 2 H 5 ) -, -CH ( CH 3 ) CH 2 -, -CH 2 CH (CH 3 ) -, -CH (CH 3 ) CH 2 CH 2 -, -C (CH 3 ) 2 -,
-CH2C(CH3)2-, -CH2CH(CH3)CH2-, -CH(CH3)-CH(CH3)-, -CH(C2H5)CH2CH2-;-CH 2 C (CH 3 ) 2 -, -CH 2 CH (CH 3 ) CH 2 -, -CH (CH 3 ) -CH (CH 3 ) -, -CH (C 2 H 5 ) CH 2 CH 2 -;
-CH2O-, -CH2S-, -(CH2)2O-, -(CH2)2S-, -CH(CH3)CH2O-, -CH(C2H5)CH2O-;-CH 2 O-, -CH 2 S-, - (CH 2 ) 2 O-, - (CH 2 ) 2 S-, -CH (CH 3 ) CH 2 O-, -CH (C 2 H 5 ) CH 2 O-;
-CH2OCH2-, CH2SCH2-, -CH(CH3)CH2OCH2-, -CH(C2H5)CH2OCH2-;-CH 2 OCH 2 -, CH 2 SCH 2 -, -CH (CH 3 ) CH 2 OCH 2 -, -CH (C 2 H 5 ) CH 2 OCH 2 -;
-CH=CH-, -C(CH3)=CH, -CH2-CH=CH-, -CH2-C(CH3)=CH-, -C≡C- -CH2-C≡C-, -CH(CH3)-C≡C-; -CH2-N(CH3)-, -(CH2)2-N(CH3)-, -(CH2)3-N(CH3)-, -CH2-N(C2H5)-, -(CH2)2-N(C2H5)-, -(CH2)3-N(C2H5)-, -CH2-N(CH3)-CH2-,-CH = CH-, -C (CH 3 ) = CH, -CH 2 -CH = CH-, -CH 2 -C (CH 3 ) = CH-, -C≡C- -CH 2 -C≡C- , -CH (CH 3 ) -C≡C-; -CH 2 -N (CH 3 ) -, - (CH 2 ) 2 -N (CH 3 ) -, - (CH 2 ) 3 -N (CH 3 ) -, -CH 2 -N (C 2 H 5 ) -, - (CH 2 ) 2 -N (C 2 H 5 ) -, - (CH 2 ) 3 -N (C 2 H 5 ) -, -CH 2 -N (CH 3 ) -CH 2 -,
-(CH2)2-N(CH3)-CH2-, -(CH2)3-N(CH3)-CH2-, -CH2-N(C2H5)-CH2-, -(CH2)2-N(C2H5)-CH2-, -(CH2)3-N(C2H5)-CH2-.- (CH 2 ) 2 -N (CH 3 ) -CH 2 -, - (CH 2 ) 3 -N (CH 3 ) -CH 2 -, -CH 2 -N (C 2 H 5 ) -CH 2 -, - (CH 2 ) 2 -N (C 2 H 5 ) -CH 2 -, - (CH 2 ) 3 -N (C 2 H 5 ) -CH 2 -.
Y steht besonders bevorzugt für eine Einfachbindung sowie für dieY particularly preferably stands for a single bond and for
Gruppierungen -OCH2-, -O(CH2)2-, -O(CH2)3-, -O(CH2)4-, -OCH(CH3)-, -OCH(C2H5)-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(C2H5)CH2-, -OCH(CH3)CH2CH2-, -OCH(C2H5)CH2CH2-, -OCH2CH(CH3)CH2-, -OCH2CH2CH(CH3)-, -OCH2CH2O-, -OCH2CH2S-, -OCH2CH2SO-, -OCH2CH2SO2-,Groupings -OCH 2 -, -O (CH 2 ) 2 -, -O (CH 2 ) 3 -, -O (CH 2 ) 4 -, -OCH (CH 3 ) -, -OCH (C 2 H 5 ) - , -OCH (CH 3 ) CH 2 -, -OCH 2 CH (CH 3 ) -, -OCH (C 2 H 5 ) CH 2 -, -OCH (CH 3 ) CH 2 CH 2 -, -OCH (C 2 H 5 ) CH 2 CH 2 -, -OCH 2 CH (CH 3 ) CH 2 -, -OCH 2 CH 2 CH (CH 3 ) -, -OCH 2 CH 2 O-, -OCH 2 CH 2 S-, - OCH 2 CH 2 SO-, -OCH 2 CH 2 SO 2 -,
-OCH(CH3)CH2O-, -OCH(C2H5)CH2O-, -OCH(CH3)CH2S-, -OCH(C2H5)CH2S-, -OCH2CH2OCH2-, -OCH2CH2SCH2-, -OCH(CH3)CH2OCH2-, -OCH(CH3)CH2SCH2-, -OCH(C2H5)CH2OCH2-, -OCH(C2H5)CH2SCH2-.-OCH (CH 3 ) CH 2 O-, -OCH (C 2 H 5 ) CH 2 O-, -OCH (CH 3 ) CH 2 S-, -OCH (C 2 H 5 ) CH 2 S-, -OCH 2 CH 2 OCH 2 -, -OCH 2 CH 2 SCH 2 -, -OCH (CH 3 ) CH 2 OCH 2 -, -OCH (CH 3 ) CH 2 SCH 2 -, -OCH (C 2 H 5 ) CH 2 OCH 2 -, -OCH (C 2 H 5 ) CH 2 SCH 2 -.
Die besonders bevorzugten Definitionen beinhalten die Maßgabe, daß für R = CN und R2 = H die Verbindungen, in welchenThe particularly preferred definitions contain the proviso that for R = CN and R 2 = H the compounds in which
R1 = C2H5 und R3 = — (/ \ bzw.R 1 = C 2 H 5 and R 3 = - (/ \ or
R1 = i-C3H7 und R3 = — ~ -CH,R 1 = iC 3 H 7 and R 3 = - ~ -CH,
ausgenommen sind.with exception of.
R steht ganz besonders bevorzugt für Cyano oder Nitro.R very particularly preferably represents cyano or nitro.
R1 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder i- Propyl, Cyclopropyl oder Phenyl.R 1 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, cyclopropyl or phenyl.
R2 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder i- Propyl oder Cyclopropyl.R 2 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl or cyclopropyl.
R3 steht ganz besonders bevorzugt die GruppierungenR 3 very particularly preferably represents the groupings
R4 -C-X-R6 , -Y-R7 und _0_R8, R5 R 4 -CXR 6 , -YR 7 and _ 0 _R 8 , R 5
wobeiin which
R4 und R5 unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder i-Propyl sowie Cyclopropyl stehen. R6 und R7 unabhängig voneinander ganz besonders bevorzugt für gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl oder Naphthyl stehen, wobei als Substituenten genannt seien:R 4 and R 5 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, n- or i-propyl and cyclopropyl. R 6 and R 7 independently of one another very particularly preferably represent phenyl or naphthyl which may be monosubstituted to trisubstituted identically or differently, the following being mentioned as substituents:
Cyano, Nitro, Amino, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i- Propyl, n-, i-, s- oder t-Butyl, Methoxy, Ethoxy, n- oder i-Propoxy, Trifluormethyl, Difluormethyl, Trifluormethoxy, Difluormethoxy, Tri- fluormethylthio, Methylamino, Dimethylamino, Acetyl, Propionyl, Methoxycarbonyl, Ethoxycarbonyl, Methylthio, Methylsulfinyl,Cyano, nitro, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, difluoromethyl , Trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methylamino, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl,
Methylsulfonyl, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylaminocarbonyl und Diethylamino- carbonyl; sowie jeweils gegebenenfalls durch Cyano, Nitro, Fluor, Chlor, Methyl, Methoxy, Methylthio, Methylsulfinyl, Methylsulfonyl, Trifluormethyl oder Trifluormethoxy, Trifluormethylthio,Methylsulfonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl and diethylaminocarbonyl; and in each case optionally by cyano, nitro, fluorine, chlorine, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl or trifluoromethoxy, trifluoromethylthio,
Trifluormethylsulfinyl oder Trifluorme hylsulfonyl substituiertes Phenyl, Phenoxy, Phenylthio, Phenylsulfinyl, Phenylsulfonyl, Benzyl oder Phenylamino; ferner für jeweils gegebenenfalls einfach bis dreifach, gleich oder verschieden durch Fluor, Chlor, Methyl, Ethyl, i-Propyl, Methoxy,Trifluoromethylsulfinyl or trifluoromethylsulfonyl substituted phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzyl or phenylamino; furthermore each for optionally single to triple, identical or different by fluorine, chlorine, methyl, ethyl, i-propyl, methoxy,
Ethoxy, Trifluormethyl oder Trifluormethoxy substituiertes Cyclo- pentan oder Cyclohexan stehen; sowie für die folgenden, gegebenenfalls einfach bis fünffach, gleich oder verschieden substituierten Heterocyclen stehen:Ethoxy, trifluoromethyl or trifluoromethoxy substituted cyclopentane or cyclohexane; and for the following heterocycles which may be monosubstituted to pentasubstituted by identical or different substituents:
wobei als (zusätzliche) Substituenten genannt seien: Cyano, Nitro, Fluor, Chlor, Brom, Methyl, Ethyl, n- oder i-Propyl, Methoxy, Trifluormethyl oder Dimethylamino oder gegebenenfalls substituiertes Phenyl, wobei als Substituenten für den Phenylrest die Substituenten in Frage kommen, die auch unter R6 für den Phenylrest genannt sind.where (additional) substituents may be mentioned: cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, trifluoromethyl or dimethylamino or optionally substituted phenyl, the substituents being suitable for the phenyl radical come, which are also mentioned under R 6 for the phenyl radical.
R8 ganz besonders bevorzugt für Methyl, Ethyl, n- oder i-Propyl; n-, i-, s- oder t-Butyl oder für gegebenenfalls einfach bis dreifach, gleich oder verschieden substituiertes Phenyl steht, wobei als Substituenten die bei R6 genannten Phenylsubstituenten infrage kommen.R 8 very particularly preferably for methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl or phenyl which is optionally monosubstituted to trisubstituted identically or differently, the phenyl substituents mentioned for R 6 being suitable as substituents.
X steht ganz besonders bevorzugt für eine Einfachbindung sowie für dieX very particularly preferably stands for a single bond and for
Gruppierungen: -CH2-, -(CH2)2-, -(CH2)3-, -CH(CH3 , -C(CH3)2-, -CH2C(CH3)2-, -CH(CH3)CH2-, -CH2O-, -CH2S-, -(CH2)2O-, -(CH2)2S-, -CH2OCH2-, CH2SCH2-, -C(CH3)=CH, -C≡C-, -(CH2)3-N(CH3)-, -(CH2)3-N(C2H5)-, -(CH2)3-N(CH3)-CH2-, -(CH2)3-N(C2H5)-CH2-. Y steht ganz besonders bevorzugt für eine Einfachbindung sowie für dieGroupings: -CH 2 -, - (CH 2 ) 2 -, - (CH 2 ) 3 -, -CH (CH 3 , -C (CH 3 ) 2 -, -CH 2 C (CH 3 ) 2 -, - CH (CH 3 ) CH 2 -, -CH 2 O-, -CH 2 S-, - (CH 2 ) 2 O-, - (CH 2 ) 2 S-, -CH 2 OCH 2 -, CH 2 SCH 2 -, -C (CH 3 ) = CH, -C≡C-, - (CH 2 ) 3 -N (CH 3 ) -, - (CH 2 ) 3 -N (C 2 H 5 ) -, - (CH 2 ) 3 -N (CH 3 ) -CH 2 -, - (CH 2 ) 3 -N (C 2 H 5 ) -CH 2 -. Y very particularly preferably stands for a single bond and for
GruppierungenGroupings
-OCH2-, -O(CH2)2-, -O(CH2)3-, -O(CH2)4-, -OCH(CH3)-, -OCH(C2H5)-, -OCH(CH3)CH2-, -OCH(CH3)CH2CH2-, -OCH(C2H5)CH2CH2-, -OCH2CH2O-, -OCH2CH2S-,-OCH 2 -, -O (CH 2 ) 2 -, -O (CH 2 ) 3 -, -O (CH 2 ) 4 -, -OCH (CH 3 ) -, -OCH (C 2 H 5 ) -, -OCH (CH 3 ) CH 2 -, -OCH (CH 3 ) CH 2 CH 2 -, -OCH (C 2 H 5 ) CH 2 CH 2 -, -OCH 2 CH 2 O-, -OCH 2 CH 2 S -,
-OCH2CH2SO-, -OCH2CH2SO2-, -OCH(CH3)CH2O-, -OCH(C2H5)CH2O-, -OCH(CH3)CH2S-, -OCH(C2H5)CH2S-, -OCH2CH2OCH2-, -OCH2CH2SCH2-.-OCH 2 CH 2 SO-, -OCH 2 CH 2 SO 2 -, -OCH (CH 3 ) CH 2 O-, -OCH (C 2 H 5 ) CH 2 O-, -OCH (CH 3 ) CH 2 S -, -OCH (C 2 H 5 ) CH 2 S-, -OCH 2 CH 2 OCH 2 -, -OCH 2 CH 2 SCH 2 -.
Die ganz besonders bevorzugten Definitionen beinhalten die Maßgabe, daß für R =The very particularly preferred definitions contain the proviso that for R =
CN und R2 = H die Verbindungen, in welchenCN and R 2 = H the compounds in which
Ri = n-C - 1H 'q9 und R3 = bzw. R i = nC - 1 H ' q 9 and R 3 = or
R1 = C,H5 und R3 = — ~ bzw.R 1 = C, H 5 and R 3 = - ~ or
R1 = CH, und R3 = — bzwR 1 = CH, and R 3 = - or
ausgenommen sind. Bevorzugte erfindungsgemäße Verbindungen sind Stoffe der Formeln (I a) bis (I h):with exception of. Preferred compounds according to the invention are substances of the formulas (I a) to (I h):
in welchenin which
R1, R2, R3, R4, R5, R6, R7, R8, X und Y für die oben genannten allgemeinen, be- vorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen.R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , X and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
Besonders hervorgehoben sind dabei die Verbindungen der obigen Formel (Ib).The compounds of the above formula (Ib) are particularly emphasized.
Bevorzugte erfindungsgemäße Verbindungen sind auch Stoffe der Formeln (I A) bisPreferred compounds according to the invention are also substances of the formulas (I A) to
(I W): (IW):
NC— N= NC - N =
NC— N=C-NH-R3 NC— N=C- -N — RJ NC— N = C-NH-R 3 NC— N = C- -N - R J
(ID) I i-C3H7 C3H7- (10)(ID) I iC 3 H 7 C 3 H 7 - (10)
C2H5 C 2 H 5
NC— N=C-NH-R3 NC - N = C-NH-R 3
in welchenin which
R3, R4, R5 und R6 für die oben genannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen steht.R 3 , R 4 , R 5 and R 6 represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
Bevorzugte erfindungsgemäße Verbindungen sind weiterhin Stoffe der Formeln (I-l) bis (1-56)Preferred compounds according to the invention are also substances of the formulas (I-I) to (1-56)
NC— N=C ι N I — CH^ 2 -R° i 1 --,. (1-3)NC - N = C ι NI - CH ^ 2 -R ° i 1 - ,. (1-3)
R1 R'R 1 R '
NC— N=C— N-CH(CH,)-CHτ-R6 NC - N = C - N - CH (CH,) - CHτ-R 6
(1-8) R1 R2 (1-8) R 1 R 2
NC— N=C— N-CH(CH3)-CH2CH— R6 NC - N = C - N - CH (CH 3 ) - CH 2 CH - R 6
(1-12) R1 R2 (1-12) R 1 R 2
NC— N=C— N— OCH(CH3)CH2CH— R7 1 1 o (1-14)NC - N = C - N - OCH (CH 3 ) CH 2 CH - R 7 1 1 o (1-14)
R1 R2 R 1 R 2
NC— N=C— N— CHj. — (CH 2,)'Z -Rb (1-15)NC - N = C - N - CHj. - (CH 2,) 'Z -R b (1-15)
R R2 RR 2
NC— N=C— N-CH(CH3)— (CH2)— R6 NC - N = C - N - CH (CH 3 ) - (CH 2 ) - R 6
(1-16) R1 R2 (1-16) R 1 R 2
NC— N=C— N-OCH(CH3)CH2O— R7 1 (1-20)NC— N = C— N-OCH (CH 3 ) CH 2 O— R 7 1 (1-20)
R1 R2 R 1 R 2
NC— N=C I — NI -CH 2— CH, 2S— RD NC - N = CI - NI - CH 2 - CH, 2S - R D
(1-21)(1-21)
R R2 RR 2
NC— N=C— N-O(CH2)2SO-R7 NC - N = C - NO (CH 2 ) 2 SO-R 7
9 (1-27)9 (1-27)
R1 R2 R 1 R 2
NC— N=C— N-O(CH2)2SO2-R7 NC - N = C - NO (CH 2 ) 2 SO 2 -R 7
9 (1-31)9 (1-31)
R1 R2 R 1 R 2
NC— N=C— N-CH(CH3)-CH2OCH— R6 NC - N = C - N - CH (CH 3 ) - CH 2 OCH - R 6
I 1 I 9 (1-34)I 1 I 9 (1-34)
R1 R2 J R 1 R 2 J
NC— N=C— N-CH(CH — CH,SCH -R6 NC - N = C - N - CH (CH - CH, SCH - R 6
R I , R L2 (I"36) RI, RL 2 (I "36)
NC— N=C— N-CH(CH,)— CH,SOCH R6 1 ' 9 (1-38) NC— N = C— N-CH (CH,) - CH, SOCH R 6 1 '9 (1-38)
R R2 RR 2
NC— N=C— N-CH(CH3)— CH2CH2S — R6 NC - N = C - N - CH (CH 3 ) - CH 2 CH 2 S - R 6
(1-44) R1 R2 (1-44) R 1 R 2
NC— N=C— N-CH -CH2N(CH3)— Rb (1-49)NC— N = C— N-CH -CH 2 N (CH 3 ) - R b (1-49)
R1 R2 R 1 R 2
NC— N=C— N-CHr-N(C,H -R6 NC - N = C - N - CHr - N (C, H - R 6
I , l 2 (1-50)I, l 2 (1-50)
NC— N=C— N-CH2— CH2CH2N(CH3)-R6 NC - N = C - N - CH 2 - CH 2 CH 2 N (CH 3 ) -R 6
(1-51) R1 R2 (1-51) R 1 R 2
NC— N=C— N-CH— CH2N(C2H5)CH R6 NC - N = C - N - CH - CH 2 N (C 2 H 5 ) CH R 6
JL l 9 (1-54)JL l 9 (1-54)
R R2 RR 2
NC— N=C— N-CH— CH2CH2N(CH3)CH R6 1 I 9 (1-55)NC— N = C— N-CH— CH 2 CH 2 N (CH 3 ) CH R 6 1 I 9 (1-55)
R R2 RR 2
in welchenin which
R1, R2, R6 und R7 für die oben genannten allgemeinen, bevorzugten, besonders bevorzugten und ganz besonders bevorzugten Bedeutungen stehen.R 1 , R 2 , R 6 and R 7 stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen gelten für die Endprodukte und für die Ausgangs- und Zwischenprodukte entsprechend. Diese Restedefinitionen können untereinander, also auch zwischen den jeweiligen Vorzugsbereichen, beliebig kombiniert werden.The general or preferred radical definitions or explanations listed above apply to the end products and to the starting and intermediate products accordingly. These residual definitions can be combined with one another, i.e. also between the respective preferred areas.
Erfindungsgemäß bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als bevorzugt (vorzugsweise) aufgeführten Be- deutungen vorliegt.According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred (preferred).
Erfindungsgemäß besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegt. 00/03976According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred. 00/03976
- 23 -- 23 -
Erfindungsgemäß ganz besonders bevorzugt werden die Verbindungen der Formel (I), in welchen eine Kombination der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegt.According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.
In den oben und nachstehend aufgeführten Restedefinitionen sind Kohlenwasserstoffreste, wie Alkyl oder Alkenyl - auch in Verbindung mit Heteroatomen wie Alkoxy oder Alkyl thio - soweit möglich jeweils geradkettig oder verzweigt.In the radical definitions given above and below, hydrocarbon radicals, such as alkyl or alkenyl - also in connection with heteroatoms, such as alkoxy or alkyl thio - are in each case straight-chain or branched as far as possible.
Im einzelnen seien die folgenden Verbindungen genannt:The following connections are specifically mentioned:
Tabelle 1Table 1
Verbindungen der Tabelle 1 entsprechen der allgemeinen Formel (I b), in welcher R1 = CH3 Compounds in Table 1 correspond to the general formula (I b), in which R 1 = CH 3
R2 = HR 2 = H
C(R4, R5) = CH2 C (R 4 , R 5 ) = CH 2
XR6 = wie im folgenden aufgelistet:XR 6 = as listed below:
Tabelle 1 (Fortsetzung) Table 1 (continued)
Tabelle 1 (Fortsetzung) Table 1 (continued)
00/03976 00/03976
■26- ■ 26-
Tabelle 1 (Fortsetzung)Table 1 (continued)
Tabelle 2Table 2
Verbindungen der Tabelle 2 entsprechen der allgemeinen Formel (I b), in welcher C(R4, R5) = CH(CH3) R!,R2undXR6 = wie in Tabelle 1 aufgelistet. 00/03976 _ 27 -Compounds in Table 2 correspond to the general formula (I b), in which C (R 4 , R5) = CH (CH 3 ) R ! , R 2 and XR 6 = as listed in Table 1. 00/03976 _ 27 -
Tabelle 3Table 3
Verbindungen der Tabelle 3 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Table 3 correspond to the general formula (I b), in which
C(R4, R5) = CH(C2H5)C (R 4 , R5) = CH (C 2 H 5 )
R1, R2 und XR6 = wie in Tabelle 1 aufgelistet.R 1 , R 2 and XR 6 = as listed in Table 1.
Tabelle 4Table 4
Verbindungen der Tabelle 4 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Table 4 correspond to the general formula (I b), in which
C(R4, R5) - CH(C3H7-i)C (R 4 , R5) - CH (C 3 H 7 -i)
R1, R2 und XR6 = wie in Tabelle 1 aufgelistet.R 1 , R 2 and XR 6 = as listed in Table 1.
Tabelle 5Table 5
Verbindungen der Tabelle 5 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Table 5 correspond to the general formula (I b), in which
C(R4, R5) = CH(C3H7-n)C (R 4 , R 5 ) = CH (C 3 H 7 -n)
R1, R2 und XR6 = wie in Tabelle 1 aufgelistet.R 1 , R 2 and XR 6 = as listed in Table 1.
Tabelle 6Table 6
Verbindungen der Tabelle 6 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Table 6 correspond to the general formula (I b), in which
C(R4, R5) = C(CH3)2 C (R 4 , R 5 ) = C (CH 3 ) 2
R1, R2 und XR6 = wie in Tabelle 1 aufgelistet.R 1 , R 2 and XR 6 = as listed in Table 1.
Tabellen 7 - 12Tables 7-12
Verbindungen der Tabellen 7 - 12 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 7-12 correspond to the general formula (Ib), in which
Rl = C2H5 Rl = C 2 H 5
R2 - HR 2 - H
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 13 - 18Tables 13-18
Verbindungen der Tabellen 13 - 18 entsprechen der allgemeinen Formel (I b), in welcher 00/03976 - 28 -Compounds in Tables 13-18 correspond to the general formula (Ib), in which 00/03976 - 28 -
Ri = C3H7-iR i = C 3 H 7 -i
R2 = HR 2 = H
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 19 - - 24Tables 19 - - 24
Verbindungen der Tabellen 19 - 24 entsprechen der allgemei in welcherConnections in Tables 19 - 24 correspond to the general ones
Rl = C3H7-nRl = C 3 H 7 -n
R2 - HR 2 - H
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 25 - 30Tables 25-30
Verbindungen der Tabellen 25 - 30 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 25-30 correspond to the general formula (Ib), in which
RI -<\RI - <\
R2 = HR 2 = H
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet. XR6 = wie in Tabelle 1 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6. XR 6 = as listed in Table 1.
Tabellen 31 - 36Tables 31-36
Verbindungen der Tabellen 31 - 36 entsprechen der allgemeinen Formel (I b), in welcher R1 = HCompounds in Tables 31-36 correspond to the general formula (I b), in which R 1 = H
R2 = HR 2 = H
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 37 - 42Tables 37-42
Verbindungen der Tabellen 37 - 42 entsprechen der allgemeinen Formel (I b), 00/03976Compounds in Tables 37-42 correspond to the general formula (I b), 00/03976
29 -29 -
in welcherin which
Ri = HRi = H
R2 = CH3 R 2 = CH 3
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 43 - 48Tables 43-48
Verbindungen der Tabellen 43 -48 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 43-48 correspond to the general formula (I b), in which
Ri = HR i = H
R2 = C2H5 R 2 = C 2 H 5
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet. XR6 wie in Tabelle 1 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6. XR 6 as listed in Table 1.
Tabellen 49 - 54Tables 49-54
Verbindungen der Tabellen 49 -54 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 49-54 correspond to the general formula (I b), in which
Ri CH3 R2 = CH3 R i CH 3 R 2 = CH 3
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet. XR6 = wie in Tabelle 1 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6. XR 6 = as listed in Table 1.
Tabellen 55 - 60Tables 55-60
Verbindungen der Tabellen 55 -60 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 55-60 correspond to the general formula (I b), in which
Rl = CH3 Rl = CH 3
R2 = C2H5 R 2 = C 2H 5
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet. XR6 = wie in Tabelle 1 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6. XR 6 = as listed in Table 1.
Tabellen 61 - 66Tables 61-66
Verbindungen der Tabellen 61 -66 entsprechen der allgemeinen Formel (I b), O 00/03976Compounds in Tables 61-66 correspond to the general formula (I b), O 00/03976
- 30 -- 30 -
in welcherin which
Rl = CH3 Rl = CH 3
R2 = C3H7-iR 2 = C 3 H 7 -i
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 67 - 72Tables 67-72
Verbindungen der Tabellen 67 -72 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 67-72 correspond to the general formula (I b), in which
Rl = C2H5 R l = C 2 H 5
R2 = CH3 R 2 = CH 3
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 73 - 78Tables 73-78
Verbindungen der Tabellen 73 -78 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 73-78 correspond to the general formula (Ib), in which
Rl = C2H5 Rl = C 2 H 5
R2 = C2H5 R 2 = C 2 H 5
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 79 - 84Tables 79-84
Verbindungen der Tabellen 79 - 84 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 79-84 correspond to the general formula (Ib), in which
R1 - C3H7-iR 1 - C 3 H 7 -i
R2 = CH3 R 2 = CH 3
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 85 - 90Tables 85-90
Verbindungen der Tabellen 85 -90 entsprechen der allgemeinen Formel (I b). O 00/03976Compounds in Tables 85-90 correspond to the general formula (I b). O 00/03976
- 31 -- 31 -
in welcherin which
Rl = C3H7-iRl = C 3 H 7 -i
R2 = C2H5 R 2 = C 2 H 5
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 91 - 96Tables 91-96
Verbindungen der Tabellen 91 - 96 entsprechen der allgemeinen Formel (I b), in welcher Rl = C3H7-nCompounds in Tables 91-96 correspond to the general formula (Ib), in which R 1 = C 3 H 7 -n
R2 = CH3 R 2 = CH 3
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6.
XR6 = wie in Tabelle 1 aufgelistet.XR 6 = as listed in Table 1.
Tabellen 97 - 102Tables 97-102
Verbindungen der Tabellen 97 - 102 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 97-102 correspond to the general formula (Ib), in which
Rl = C3H7-n R2 = C2H5 R l = C 3 H 7 -n R 2 = C 2 H 5
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet. XR6 = wie in Tabelle 1 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6. XR 6 = as listed in Table 1.
Tabellen 103 - 108Tables 103-108
Verbindungen der Tabellen 103 - 108 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 103-108 correspond to the general formula (Ib), in which
'Rl 'R l
R2 = CH3 R 2 = CH 3
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet. XR6 = wie in Tabelle 1 aufgelistet. O 00/03976 32C (R 4 , R 5 ) = as listed in Tables 1 to 6. XR 6 = as listed in Table 1. O 00/03976 32
Tabellen 109 - 114Tables 109-114
Verbindungen der Tabellen 109 -114 entsprechen der allgemeinen Formel (I b), in welcherCompounds in Tables 109-114 correspond to the general formula (Ib), in which
Rl →R l →
R2 = C2H5 R 2 = C 2 H 5
C(R4, R5) = wie in den Tabellen 1 bis 6 aufgelistet. XR6 = wie in Tabelle 1 aufgelistet.C (R 4 , R 5 ) = as listed in Tables 1 to 6. XR 6 = as listed in Table 1.
Tabelle 115Table 115
Verbindungen der Tabelle 115 entsprechen der allgemeinen Formel (I c), in welcherCompounds in Table 115 correspond to the general formula (I c), in which
Rl CH3 R2 H YR7 wie im folgenden aufgelistet:R l CH 3 R 2 H YR 7 as listed below:
Tabelle 115 (Fortsetzung) Table 115 (continued)
Tabelle 116Table 116
V Λindunge„ der Tabelle , „ entsprechen der aπgemeinen Fome| ^ h Connection e "of the table ," correspond to the general form | ^ h
Ri = C2H5 R2 = H YR7 wie in Tabelle 1 15 aufgelistet. 00/03976 - 34 -R i = C 2 H 5 R 2 = H YR 7 as listed in Table 1 15. 00/03976 - 34 -
Tabelle 117Table 117
Verbindungen der Tabelle 117 entsprechen der allgemeinen Formel (I c), in welcher Rl - C3H7-iCompounds in Table 117 correspond to the general formula (I c), in which R 1 - C 3 H 7 -i
R2 = H YR7 = wie in Tabelle 115 aufgelistet.R 2 = H YR 7 = as listed in Table 115.
Tabelle 118Table 118
Verbindungen der Tabelle 118 entsprechen der allgemeinen Formel (I c), in welcher Rl = C3H7-n R2 . = HCompounds in Table 118 correspond to the general formula (I c), in which R 1 = C 3 H 7 -n R 2 . = H
YR7 = wie in Tabelle 115 aufgelistet.YR 7 = as listed in Table 115.
Tabelle 119Table 119
Verbindungen der Tabelle 119 entsprechen der allgemeinen Formel (I c), in welcherCompounds in Table 119 correspond to the general formula (I c), in which
Rl = -ORl = -O
R2 = HR 2 = H
YR7 = wie in Tabelle 115 aufgelistet.YR 7 = as listed in Table 115.
Tabelle 120 Verbindungen der Tabelle 120 entsprechen der allgemeinen Formel (I c), in welcherTable 120 Compounds in Table 120 correspond to the general formula (I c), in which
R> = HR> = H
R2 = HR 2 = H
YR7 = wie in Tabelle 115 aufgelistet.YR 7 = as listed in Table 115.
Tabelle 121Table 121
Verbindungen der Tabelle 121 entsprechen der allgemeinen Formel (I c), in welcherCompounds in Table 121 correspond to the general formula (I c), in which
Rl = HRl = H
R2 = CH3 R 2 = CH 3
YR7 = wie in Tabelle 1 15 auf Ageelistet. 00/03976 _ 35 _YR 7 = as listed in Table 1 15 on A. 00/03976 _ 35 _
Tabelle 122Table 122
Verbindungen der Tabelle 122 entsprechen der allgemeinen Formel (I c), in welcher Rl = HCompounds in Table 122 correspond to the general formula (I c), in which Rl = H
R2 = C2H5 YR7 = wie in Tabelle 115 aufgelistet.R 2 = C 2 H 5 YR 7 = as listed in Table 115.
Tabelle 123Table 123
Verbindungen der Tabelle 123 entsprechen der allgemeinen Formel (I c), in welcher Rl = H R2 = C3H7-iCompounds in Table 123 correspond to the general formula (I c), in which R 1 = HR 2 = C 3 H 7 -i
YR7 = wie in Tabelle 1 15 aufgelistet.YR 7 = as listed in Table 1 15.
Tabelle 124Table 124
Verbindungen der Tabelle 124 entsprechen der allgemeinen Formel (I c), in welcher Rl = CH3 Compounds in Table 124 correspond to the general formula (I c), in which R 1 = CH 3
R2 = CH3 R 2 = CH 3
YR7 = wie in Tabelle 115 aufgelistet.YR 7 = as listed in Table 115.
Tabelle 125 Verbindungen der Tabelle 125 entsprechen der allgemeinen Formel (I c), in welcherTable 125 Compounds in Table 125 correspond to the general formula (I c), in which
Rl = CH3 R l = CH 3
R2 = C2H5 R 2 = C 2 H 5
YR7 = wie in Tabelle 115 aufgelistet.YR 7 = as listed in Table 115.
Tabelle 126Table 126
Verbindungen der Tabelle 126 entsprechen der allgemeinen Formel (I c), in welcherCompounds in Table 126 correspond to the general formula (I c), in which
Rl = CH3 R l = CH 3
R2 = C3H7-iR 2 = C 3 H 7 -i
YR7 - wie in Tabelle 1 15 aufgelistet. Tabelle 127YR 7 - as listed in Table 1 15. Table 127
Verbindungen der Tabelle 127 entsprechen der allgemeinen Formel (I c), in welcher Ri = C2H5 Compounds in Table 127 correspond to the general formula (I c), in which Ri = C 2 H 5
R2 = CH3 YR7 = wie in Tabelle 115 aufgelistet.R 2 = CH 3 YR 7 = as listed in Table 115.
Tabelle 128Table 128
Verbindungen der Tabelle 128 entsprechen der allgemeinen Formel (I c), in welcher Rl - C2H5 R2 = C2H5 Compounds in Table 128 correspond to the general formula (I c), in which R 1 - C 2 H 5 R 2 = C 2 H 5
YR7 = wie in Tabelle 115 aufgelistet.YR 7 = as listed in Table 115.
Tabelle 129Table 129
Verbindungen der Tabelle 129 entsprechen der allgemeinen Formel (I c), in welcher Rl = C3H7-iCompounds in Table 129 correspond to the general formula (I c), in which R 1 = C 3 H 7 -i
R2 = CH3 R 2 = CH 3
YR7 = wie in Tabelle 1 15 aufgelistet.YR 7 = as listed in Table 1 15.
Tabelle 130 Verbindungen der Tabelle 130 entsprechen der allgemeinen Formel (I c), in welcherTable 130 Compounds in Table 130 correspond to the general formula (I c), in which
Rl = C3H7-iR l = C 3 H 7 -i
R2 = C2H5 R 2 = C 2 H 5
YR7 = wie in Tabelle 115 aufgelistet.YR 7 = as listed in Table 115.
Tabelle 131Table 131
Verbindungen der Tabelle 131 entsprechen der allgemeinen Formel (I c), in welcher Rl = CH3 Compounds in Table 131 correspond to the general formula (I c), in which R 1 = CH 3
R2 - -R 2 - -
YR7 = wie in Tabelle 115 aufgelistet Bevorzugt genannt seien die folgenden Verbindungen: Tabelle aYR 7 = as listed in Table 115 The following compounds are preferred: Table a
Ri R2 R4 R5 X 6R i R2 R4 R5 X 6
3 H H CH3 -CFI2CH2- /= CF3 3 HH CH 3 -CFI 2 CH 2 - / = CF3
CH3 H H CH3 -CH2CH2- — 0~CH3CH 3 HH CH 3 -CH 2 CH 2 - - 0 ~ CH 3
CH3 H H ClCH 3 HH Cl
CH3 -CH2CH2-CH 3 -CH 2 CH 2 -
~ ~cι~ ~ cι
CH, H CH, CH3 -CH2CH2- \JCH, H CH, CH 3 -CH 2 CH 2 - \ J
CH3 H CH3 CH3 -CH2CH2- /=<Cl CH3 H CH 3 CH 3 -CH 2 CH 2 - / = < Cl
CH,CH,
H CH3 CH3 -CH2CH2- ~ ~CH H CH 3 CH 3 -CH 2 CH 2 - ~ ~ CH
CH^ H CH3 CH3 -CH2CH2- —Cl CH ^ H CH 3 CH 3 -CH 2 CH 2 - - Cl
\J-a \ J- a
Tabelle ε ι (Fortsetzung) Table ε ι (continued)
Ri R2 R4 R5 X R6R i R2 R4 R5 X R6
CH3 H H CH3 -CH(CH3)CH2-CH 3 HH CH 3 -CH (CH 3 ) CH 2 -
CH3 H H CH3 ClCH 3 HH CH 3 Cl
-CH(CH3)CH2--CH (CH 3 ) CH 2 -
CH3 H H CH3 -CH(CH3)CH2- - -cι CH 3 HH CH 3 -CH (CH 3 ) CH 2 - - - cι
CH3 H H CH3 -CH(CH3)CH2- ~ -F CH 3 HH CH 3 -CH (CH 3 ) CH 2 - ~ - F
CH3 H H CH3 -CH(CH3)CH2- — ~Br CH 3 HH CH 3 -CH (CH 3 ) CH 2 - - ~ Br
CH3 H H CH3 -CH(CH3)CH2- CH 3 HH CH 3 -CH (CH 3 ) CH 2 -
CH3 H H H -CH(CH3)CH2- ~ "cι CH 3 HHH -CH (CH 3 ) CH 2 - ~ " cι
CH3 H H H -CH(CH3)CH2- -Λ cι CH 3 HHH -CH (CH 3 ) CH 2 - -Λ cι
CH3 H H CH3 -(CH2)3N(CH3)- CH 3 HH CH 3 - (CH 2 ) 3 N (CH 3 ) -
CH3 H H CH3 -(CH2)3N(C2H5)- Q 3 H H H -CH(CH3)-CH 3 HH CH 3 - (CH 2 ) 3 N (C 2 H 5 ) - Q 3 HHH -CH (CH 3 ) -
CH3 H H H ClCH 3 HHH Cl
-CH(CH3)--CH (CH 3 ) -
CH3 H H H -CH(CH3)-CH 3 HHH -CH (CH 3 ) -
CH3 H -o^α CH 3 H -o ^ α
H H -CH(CH3)- —ζ ~F HH -CH (CH 3 ) - —ζ ~ F
CH3 H H H -CH(CH3)- — 0^Br Tabelle ∑ i (Fortsetzung)CH 3 HHH -CH (CH 3 ) - - 0 ^ Br Table ∑ i (continued)
Rl R2 R4 R5 X R6Rl R 2 R 4 R5 X R6
CH3 H H H -CH(CH3)- - -CF3CH 3 HHH -CH (CH 3 ) - - - CF 3
CH3 H CH3 CH3 -C≡C- ϊ?CH 3 H CH 3 CH 3 -C≡C- ϊ?
CH3 H H CH3 - χθCH 3 HH CH 3 - χθ
CH, H HX^__CH, H HX ^ __
H CH, -CH2O-H CH, -CH 2 O-
Tabelle z t (Fortsetzung) Table currently (continued)
Rl R2 R4 R5 X R6R l R 2 R 4 R5 X R6
CH3 H ClCH 3 H Cl
CH3 CH3 -C=C-CH 3 CH 3 -C = C-
CH3 H CH3 CH3 -CsC- — "cι CH 3 H CH 3 CH 3 -CsC- - "cι
CH3 H CH3 CH3 -C≡C- r- Cl CH 3 H CH 3 CH 3 -C≡C- r- Cl
CH3 H CH3 CH3 -G≡C- - CN CH 3 H CH 3 CH 3 -G≡C- - CN
CH3 H CH3 CH3 -C≡C- -θ-C(CH3)3CH 3 H CH 3 CH 3 -C≡C- -θ- C (CH 3 ) 3
CH3 H CH3 CH3 -C≡C- - ~CF3CH 3 H CH 3 CH 3 -C≡C- - ~ CF 3
CH3 H CH3 CH3 -C≡C- — "CH3CH 3 H CH 3 CH 3 -C≡C- - "CH 3
CH3 H CH3 CH3 -CsC- - -F 3 H H CH3 -CH2- — Oc< CH 3 H CH 3 CH 3 -CsC- - - F 3 HH CH 3 -CH 2 - - O c <
Tabelle bTable b
Tabelle b (Fortsetzung) Table b (continued)
Tabelle cTable c
R6 = vvie in Tabelle b aufgeführt, sowie zusätzlichR6 = vvie listed in table b, as well as additional
Tabelle dTable d
R6 = wie in Tabelle c aufgeführt. Tabelle eR 6 = as listed in Table c. Table e
Tabelle f Table f
R6 = wie in Tabelle e aufgeführt.R 6 = as listed in Table e.
Tabelle gTable g
Tabelle g (Fortsetzung) Table g (continued)
Tabelle hTable h
NC— N=C N— Y — R7 L.1 ' n (I c)NC— N = CN— Y - R 7 L.1 'n (I c)
R R2 RR 2
Rl R2 R7Rl R2 R7
CH3 H -Cl Die o.g. erfindungsgemäßen Verbindungen der verschiedenen Formeln und in den einzelnen Tabellen können gegebenenfalls als Racemate, R- oder S-Isomere vorliegen. Verwendet man beispielsweise N-Cyano-ethanimidsäuremethylester und 4- Chlor-2-methylbenzylamin als Ausgangsstoffe, so kann der Verlauf des erfindungsgemäßen Verfahrens durch das folgende Reaktionsschema wiedergegeben werden:CH3 H -Cl The above-mentioned compounds according to the invention of the different formulas and in the individual tables can optionally be present as racemates, R or S isomers. If, for example, methyl N-cyanoethanimidate and 4-chloro-2-methylbenzylamine are used as starting materials, the course of the process according to the invention can be represented by the following reaction scheme:
Die zur Durchführung des erfindungsgemäßen Verfahrens als Ausgangsstoffe benötigten Ethanimidsäureester sind durch die Formel (II) allgemein definiert. In dieser Formel steht Z vorzugsweise für Cι -C4-Alkyl, wie insbesondere für Methyl oder Ethyl.Formula (II) provides a general definition of the ethanimide esters required as starting materials for carrying out the process according to the invention. In this formula, Z is preferably C 4 -C 4 -alkyl, in particular methyl or ethyl.
Die N-Cyano-ethanimidsäureester sind weitgehend bekannt (vgl. z.B. US 5.304 566 oder J. Org. Chem. 28, 1963, 1816-1821) und/oder nach üblichen Verfahren erhältlich.The N-cyanoethanimidic acid esters are largely known (see, for example, US 5,304,566 or J. Org. Chem. 28, 1963, 1816-1821) and / or can be obtained by customary processes.
Die N-Nitro-ethanimidsäureester werden erhalten indem man z.B. die entsprechen- den NO2-freien Ethanimidsäureester der Formel (II) in üblicher Weise nitriert.The N-nitro-ethanimidic acid esters are obtained, for example, by nitrating the corresponding NO 2 -free ethanimidic acid esters of the formula (II) in a conventional manner.
Die weiterhin beim erfindungsgemäßen Verfahren als Ausgangsstoffe zu verwendenden Amine der allgemeinen Formel (III) sind allgemein bekannte Verbindungen der organischen Chemie bzw. in allgemein bekannter Art und Weise erhältlich. Das erfindungsgemäße Verfahren wird vorzugsweise in Gegenwart eines Verdünnungsmittels durchgeführt. Vorzugsweise verwendbar sind Alkohole, wie Methanol und Ethanol; Nitrile, wie Acetonitril oder Ester, wie Essigsäureethylester. Es ist auch möglich, gegebenenfalls in Wasser oder organisch-wässrigen Gemischen zu arbeiten.The amines of the general formula (III) to be used as starting materials in the process according to the invention are generally known compounds of organic chemistry or can be obtained in a generally known manner. The process according to the invention is preferably carried out in the presence of a diluent. Alcohols such as methanol and ethanol can preferably be used; Nitriles such as acetonitrile or esters such as ethyl acetate. It is also possible to work in water or organic-aqueous mixtures if necessary.
Bei der Durchführung des erfindungsgemäßen Verfahrens arbeitet man vorzugsweise in äquimolaren Mengen; es ist aber auch möglich, das eine oder andere Ausgangsprodukt im Überschuß einzusetzen.When carrying out the process according to the invention, one preferably works in equimolar amounts; but it is also possible to use one or the other starting product in excess.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßenThe reaction temperatures can be carried out when carrying out the process according to the invention
Verfahrens in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen zwischen 0°C und 100°C, bevorzugt zwischen 20°C und 80°C.Process can be varied over a wide range. In general, temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 80 ° C.
Aufarbeitung und Isolierung der Endprodukte erfolgen in allgemein bekannter Art und Weise.The end products are worked up and isolated in a generally known manner.
Die Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit und günstiger Warm- blütertoxizität zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, im Vorrats- und Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Pflanzenschutzmittel eingesetzt werden. Sie sind gegen normal sensible und resi- stente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:With good plant tolerance and favorable toxicity to warm-blooded animals, the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:
Aus der Ordnung der Isopoda z.B. Oniscus asellus, Armadillidium vulgäre, Porcellio scaber. Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus.From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
Aus der Ordnung der Chilopoda z.B. Geophilus carpophagus, Scutigera spp. Aus der Ordnung der Symphyla z.B. Scutigerella immaculata.From the order of the Chilopoda, for example, Geophilus carpophagus and Scutigera spp. From the order of the Symphyla, for example, Scutigerella immaculata.
Aus der Ordnung der Thysanura z.B. Lepisma saccharina.From the order of the Thysanura e.g. Lepisma saccharina.
Aus der Ordnung der Collembola z.B. Onychiurus armatus.From the order of the Collembola e.g. Onychiurus armatus.
Aus der Ordnung der Orthoptera z.B. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.From the order of the Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
Aus der Ordnung der Blattaria z.B. Blatta orientalis, Periplaneta americana,From the order of the Blattaria e.g. Blatta orientalis, Periplaneta americana,
Leucophaea maderae, Blattella germanica.Leucophaea maderae, Blattella germanica.
Aus der Ordnung der Dermaptera z.B. Forficula auricularia.From the order of the Dermaptera e.g. Forficula auricularia.
Aus der Ordnung der Isoptera z.B. Reticulitermes spp..From the order of the Isoptera e.g. Reticulitermes spp ..
Aus der Ordnung der Phthiraptera z.B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp..From the order of the Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci,From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci,
Thrips palmi, Frankliniella accidentalis.Thrips palmi, Frankliniella accidentalis.
Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.From the order of the Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigususpp. Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
Aus der Ordnung der Lepidoptera z.B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylustella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionelia, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana. Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylustella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppppi, Fitrella, Phyllocnist spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellioneliaanaellaanaellaanaellaanaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaella pellaella pellaella . Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
Aus der Ordnung der Coleoptera z.B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni,From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni,
Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatordimidhmpphppm, spp. , Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha., Amphimalltra solitus
Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp.,From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp.,
Monomorium pharaonis, Vespa spp.Monomorium pharaonis, Vespa spp.
Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Culex spp.,From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp.,
Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Flyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp..Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Flyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomy
Aus der Ordnung der Siphonaptera z.B. Xenopsylla cheopis, Ceratophyllus spp..From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..
Aus der Klasse der Arachnida z.B. Scorpio maurus, Latrodectus mactans.From the class of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.
Aus der Ordnung der Acarina z.B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,From the order of the Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp.,
Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp..Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
Zu den pflanzenparasitären Nematoden gehören z.B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursa phelenchus spp..Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursa.
Die erfindungsgemäßen Verbindungen der Formel (I) zeichnen sich insbesondere durch eine gute nematizide Wirksamkeit aus. So lassen sie sich beispielsweise mit besonders gutem Erfolg zur Bekämpfung von Meloidogyne incognita einsetzenThe compounds of the formula (I) according to the invention are notable in particular for good nematicidal activity. For example, they can be used with particularly good success to combat Meloidogyne incognita
Die Wirkstoffe können in die üblichen Formulierungen überführt werden, wie Lö- sungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.
In den entsprechenden Aufwandmengen zeigen die erfindungsgemäßen Ver- bindungen teilweise herbizide Wirkungen. Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugendenIn the corresponding application rates, the compounds according to the invention show herbicidal effects in some cases. These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents
Mitteln.Means.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkyl- naphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polareIf water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar
Lösungsmittel, wie Dimethylformamid und Dimefhylsulfoxid, sowie Wasser.Solvents, such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage:The following are suitable as solid carriers:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden,e.g. Ammonium salts and natural rock flours, such as kaolins, clays,
Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde' und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylaryl-polyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Einweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth ' and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, Alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
Der erfindungsgemäße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Bakteriziden,In its commercially available formulations and in the use forms prepared from these formulations, the active compound according to the invention can be mixed with other active compounds, such as insecticides, attractants, sterilants, bactericides,
Akariziden, Nematiziden, Fungiziden, wachstumsregulierenden Stoffen oder Herbiziden vorliegen. Zu den Insektiziden zählen beispielsweise Phosphorsäureester, Carbamate, Carbonsäureester, chlorierte Kohlenwasserstoffe, Phenylharnstoffe, durch Mikroorganismen hergestellte Stoffe u.a.Acaricides, nematicides, fungicides, growth regulators or herbicides are present. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
Besonders günstige Mischpartner sind z.B. die folgenden: Fungizide:The following are particularly favorable mixed partners: Fungicides:
Aldimoφh, Ampropylfos, Ampropylfos-Kalium, Andoprim, Anilazin, Azaconazol, Azoxystrobin,Aldimoφh, Ampropylfos, Ampropylfos Potassium, Andoprim, Anilazine, Azaconazole, Azoxystrobin,
Benalaxyl, Benodanil, Benomyl, Benzamacril, Benzamacryl-isobutyl, Bialaphos, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazol, Bupirimat, Buthiobat,Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calciumpolysulfid, Capsimycin, Captafol, Captan, Carbendazim, Carboxin, Carvon, Chinomethionat (Quinomethionat), Chlobenthiazon, Chlorfenazol, Chloroneb, Chloro- picrin, Chlorothalonil, Chlozolinat, Clozylacon, Cufraneb, Cymoxanil, Cyproconazol, Cyprodinil, Cyprofuram,Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodinconol
Debacarb, Dichlorophen, Diclobutrazol, Diclofluanid, Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethirimol, Dimethomoφh, Diniconazol,Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomoφh, diniconazole,
Diniconazol-M, Dinocap, Diphenylamin, Dipyrithione, Ditalimfos, Dithianon, Dodemoφh, Dodine, Drazoxolon,Diniconazol-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemoφh, Dodine, Drazoxolon,
Ediphenphos, Epoxiconazol, Etaconazol, Ethirimol, Etridiazol,Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadon, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Fluφrimidol, Flusilazol, Flusul- famid, Flutolanil, Flutriafol, Folpet, Fosetyl-Alminium, Fosetyl-Natrium, Fthalid, Fuberidazol, Furalaxyl, Furametpyr, Furcarbonil, Furconazol, Furconazol-cis,Famoxadon, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Fluφrimidol, Flutilanol, Flusil- fililol, Flusilanol, Flusil- fililol, Flusil- fililol, Flusil- fililol-, Flusil- fidol, Flusil- fidol, Flusil- fidil, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidil, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Flusil- fidol, Alminium, fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis,
Furmecyclox,Furmecyclox,
Guazatin,Guazatin,
Hexachlorobenzol, Hexaconazol, Hymexazol, Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobenfos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,Hexachlorobenzene, hexaconazole, hymexazole, Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, Kupfer-Zubereitungen, wie: Kupferhydroxid, Kupfemaphthenat, Kupferoxychlorid, Kupfersulfat, Kupferoxid, Oxin-Kupfer und Bordeaux-Mischung,Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,Metconazole, methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
Nickel-dimethyldithiocarbamat, Nitrothal-isopropyl, Nuarimol,Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazol, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin. Polyoxin, Polyoxorim, Probenazol, Prochloraz, Procymidon, Propamocarb, Propanosine-Natrium, Propiconazol, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil,Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin. Polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil,
Pyroquilon, Pyroxyfur,Pyroquilon, Pyroxyfur,
Quinconazol, Quintozen (PCNB),Quinconazole, quintozen (PCNB),
Schwefel und Schwefel-Zubereitungen,Sulfur and sulfur preparations,
Tebuconazol, Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazol, Thiabendazol, Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemoφh, Triflumizol, Triforin, Triticonazol, O 00/03976Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemoφh, triflumizole, triforine, triticonazole, O 00/03976
- 55- 55
Uniconazol,Uniconazole,
Validamycin A, Vinclozolin, Viniconazol,Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram sowieZarilamid, Zineb, Ziram as well
Dagger G,Dagger G,
OK-8705,OK-8705,
OK-8801,OK-8801,
α-( 1 , 1 -Dimethylethyl)-ß-(2-phenoxy ethyl)- 1 H- 1 ,2,4-triazol- 1 -ethanol,α- (1,1-dimethylethyl) -ß- (2-phenoxyethyl) -1 H-1,2,4-triazole-1-ethanol,
α-(2,4-Dichlθφhenyl)-ß-fluor-b-propyl- 1 H- 1 ,2,4-triazol- 1 -ethanol,α- (2,4-dichlorothenyl) -ß-fluoro-b-propyl-1 H-1, 2,4-triazole-1-ethanol,
α-(2,4-Dichlθφhenyl)-ß-methoxy-a-methyl- 1 H-l ,2,4-triazol- 1 -ethanol,α- (2,4-dichlorothenyl) -ß-methoxy-a-methyl-1 H-l, 2,4-triazole-1-ethanol,
α-(5-Methyl-l,3-dioxan-5-yl)-ß-[[4-(trifluormethyl)-phenyl]-methylen]-lH-l,2,4- . triazol-1 -ethanol,α- (5-Methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH-l, 2,4-. triazole-1-ethanol,
(5RS,6RS)-6-Hydroxy-2,2,7,7-tetramethyl-5-(lH-l,2,4-triazol-l-yl)-3-octanon,(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (lH-l, 2,4-triazol-l-yl) -3-octanone,
• (E)-a-(Methoxyimino)-N-methyl-2-phenoxy-phenylacetamid, • (E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
{2-Methyl-l-[[[l-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbaminsäure-l- isopropylester{2-Methyl-l - [[[l- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid l-isopropyl ester
l-(2,4-Dichlorphenyl)-2-(lH-l,2,4-triazol-l-yl)-ethanon-O-(phenylmethyl)-oxim, 1 -(2-Methyl- 1 -naphthalenyl)- 1 H-pyrrol-2,5-dion,l- (2,4-dichlorophenyl) -2- (lH-l, 2,4-triazol-l-yl) -ethanone-O- (phenylmethyl) oxime, 1 - (2-methyl-1-naphthalenyl) - 1 H-pyrrole-2,5-dione,
l-(3,5-Dichloφhenyl)-3-(2-propenyl)-2,5-pyrrolidindion,l- (3,5-dichloφhenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
l-[(Diiodmethyl)-sulfonyl]-4-methyl-benzol,l - [(diiodomethyl) sulfonyl] -4-methyl-benzene,
l-[[2-(2,4-Dichloφhenyl)-l,3-dioxolan-2-yl]-methyl]-lH-imidazol,l - [[2- (2,4-dichlorophenyl) -1, 3-dioxolan-2-yl] methyl] -1 H-imidazole,
l-[[2-(4-Chloφhenyl)-3-phenyloxiranyl]-methyl]-lH-l,2,4-triazol,l - [[2- (4-chloro-phenyl) -3-phenyloxiranyl] methyl] -lH-l, 2,4-triazole,
l-[l-[2-[(2,4-Dichloφhenyl)-methoxy]-phenyl]-ethenyl]-lH-imidazol,l- [l- [2 - [(2,4-dichloφhenyl) methoxy] phenyl] ethenyl] -lH-imidazole,
l-Methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol,l-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
2',6'-Dibrom-2-methyl-4'-trifluormethoxy-4'-trifluor-methyl-l,3-thiazol-5-carboxanilid,2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-l, 3-thiazole-5-carboxanilide,
2,2-Dichlor-N-[l-(4-chlθφhenyl)-ethyl]-l-ethyl-3-methyl-cyclopropancarboxamid,2,2-dichloro-N- [1- (4-chloro-phenyl) -ethyl] -l-ethyl-3-methyl-cyclopropanecarboxamide,
2,6-Dichlor-5-(methylthio)-4-pyrimidinyl-thiocyanat,2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,
2,6-Dichlor-N-(4-trifluormethylbenzyl)-benzamid,2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,
2,6-Dichlor-N-[[4-(trifluormethyl)-phenyl]-methyl]-benzamid,2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
2-(2,3,3-Triiod-2-propenyl)-2H-tetrazol,2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
2-[(l-Methylethyl)-sulfonyl]-5-(trichlormethyl)-l,3,4-thiadiazol, 2-[[6-Deoxy-4-O-(4-O-methyl-ß-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-4- methoxy-lH-pyrrolo[2,3-d]pyrimidin-5-carbonitril,2 - [(l-methylethyl) sulfonyl] -5- (trichloromethyl) -1, 3,4-thiadiazole, 2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4- methoxy-lH-pyrrolo [2,3-d] pyrimidine- 5-carbonitrile,
2-Aminobutan,2-aminobutane,
2-Brom-2-(brommethyl)-pentandinitril,2-bromo-2- (bromomethyl) pentandinitrile,
2-Chlor-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridincarboxamid,2-chloro-N- (2,3-dihydro-l, l, 3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamide,
2-Chlor-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamid,2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,
2-Phenylphenol(OPP),2-phenylphenol (OPP),
3,4-Dichlor-l-[4-(difluormethoxy)-phenyl]-lH-pyrrol-2,5-dion,3,4-dichloro-l- [4- (difluoromethoxy) phenyl] -IH-pyrrole-2,5-dione,
3,5-Dichlor-N-[cyan[(l-methyl-2-propynyl)-oxy]-methyl]-benzamid,3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,
3 -( 1 , 1 -Dimethy lpropyl- 1 -oxo- 1 H-inden-2-carbonitril,3 - (1,1-dimethyl propyl-1-oxo-1 H-indene-2-carbonitrile,
3-[2-(4-Chlθφhenyl)-5-ethoxy-3-isoxazolidinyl]-pyridin,3- [2- (4-Chlθφhenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
4-Chlor-2-cyan-N,N-dimethyl-5-(4-methylphenyl)-lH-imidazol-l-sulfonamid,4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -lH-imidazole-l-sulfonamide,
4-Methyl-tetrazolo[l,5-a]quinazolin-5(4H)-on,4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
8-(l,l-Dimethylethyl)-N-ethyl-N-propyl-l,4-dioxaspiro[4.5]decan-2-methanamin,8- (l, l-dimethylethyl) -N-ethyl-N-propyl-l, 4-dioxaspiro [4.5] decane-2-methanamine,
8-Hydroxychinolinsulfat,8-hydroxyquinoline sulfate,
9H-Xanthen-9-carbonsäure-2-[(phenylamino)-carbonyl]-hydrazid, bis-(l-Methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thioρhendicarboxylat,9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide, bis- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thioρhendicarboxylate,
eis- 1 -(4-Chlθφhenyl)-2-( 1 H- 1 ,2,4-triazol- 1 -yl)-cycloheptanol,Eis- 1 - (4-Chlθφhenyl) -2- (1 H- 1, 2,4-triazol-1 -yl) -cycloheptanol,
cis-4-[3-[4-(l,l-Dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-moφholin- hydrochlorid,cis-4- [3- [4- (l, l-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethyl-moφholin hydrochloride,
Ethyl-[(4-chloφhenyl)-azo]-cyanoacetat,Ethyl - [(4-chloro-phenyl) -azo] cyanoacetate,
Kaliumhydrogencarbonat,Potassium hydrogen carbonate,
Methantetrathiol-Natriumsalz,Methane tetrathiol sodium salt,
Methyl- 1 -(2,3-dihydro-2,2-dimethyl- 1 H-inden- 1 -yl)- 1 H-imidazol-5-carboxylat,Methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1-yl) - 1 H-imidazole-5-carboxylate,
Methyl-N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninat,Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Methyl-N-(chloracetyl)-N-(2,6-dimethylphenyl)-DL-alaninat,Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
N-(2,3-Dichlor-4-hydroxyphenyl)-l-methyl-cyclohexancarboxamid.N- (2,3-dichloro-4-hydroxyphenyl) -l-methyl-cyclohexane carboxamide.
N-(2,6-Dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamid,N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
N-(2,6-Dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamid,N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
N-(2-Chlor-4-nitrophenyl)-4-methyl-3-nitro-benzolsulfonamid,N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
N-(4-Cyclohexylphenyl)- 1 ,4,5 ,6-tetrahydro-2-pyrimidinamin, N-(4-Hexylphenyl)- 1 ,4,5,6-tetrahydro-2-pyrimidinamin,N- (4-cyclohexylphenyl) - 1, 4,5, 6-tetrahydro-2-pyrimidinamine, N- (4-hexylphenyl) - 1, 4,5,6-tetrahydro-2-pyrimidinamine,
N-(5-Chlor-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamid,N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide,
N-(6-Methoxy)-3-pyridinyl)-cyclopropancarboxamid,N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide,
N-[2,2,2-Trichlor- 1 -[(chloracety l)-amino]-ethyl]-benzamid,N- [2,2,2-trichloro-1 - [(chloroacety l) amino] ethyl] benzamide,
N-[3-Chlor-4,5-bis-(2-propinyloxy)-phenyl]-N'-methoxy-methanimidamid,N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxymanimidamide,
N-Formyl-N-hydroxy-DL-alanin -Natriumsalz,N-formyl-N-hydroxy-DL-alanine sodium salt,
O,O-Diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioat,O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
O-Methyl-S-phenyl-phenylpropylphosphoramidothioate,O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-Methyl- 1 ,2,3-benzothiadiazol-7-carbothioat,S-methyl-1, 2,3-benzothiadiazole-7-carbothioate,
spiro [2H] - 1 -Benzopyran-2, 1 '(3 'H)-isobenzofuran]-3 '-on,spiro [2H] - 1-benzopyran-2, 1 '(3' H) -isobenzofuran] -3 '-one,
Bakterizide:Bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Teclofta- - lam, Kupfersulfat und andere Kupfer-Zubereitungen. Insektizide / Akarizide / Nematizide:Bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, teclofta-lam, copper sulfate and other copper preparations. Insecticides / acaricides / nematicides:
Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Buto- carboxim, Butylpyridaben,Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxim, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chloφyrifos M, Cis-Resmethrin, Clocythrin, Clofen- tezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chloφyrifos M, Cis-Resmethrin, Clocythrinhrinhrinhrin, Clyanothrinhrin, Clyanothrinhrin, Clyanothrinhrin, Clyanothrinhrin, Clyanothrin, Clyanothrinhrin, Clyanothrin, Cyclin Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Di- methoat, Dimethylvinphos, Dioxathion, Disulfoton,Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoate, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,
Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,Fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,
HCH, Heptenophos, Hexaflumuron, Hexythiazox, Imidacloprid, Iprobenfos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,HCH, heptenophos, hexaflumuron, hexythiazox, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
Lambda-cyhalothrin, Lufenuron,Lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyd, Methacrifos,Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos,
Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Mübemectin, Monocrotophos, Moxidectin,Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Mübemectin, Monocrotophos, Moxidectin,
Naled, NC 184, NI 25, NitenpyramNaled, NC 184, NI 25, Nitenpyram
Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos,Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos,
Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
Quinalphos,Quinalphos,
RH 5992,RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Spinosad,Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Spinosad,
Tebufenozid, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, .Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio- methon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron, Trichlorfon, Triflumuron, Trimethacarb, Thiamethoxam,Tebufenozid, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, .Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazin, Thuringiensin, Tralomenhriazonium, Tralomenhriazon, Tronomenhrononium, Tronomenhrononium, Tronomenhriazon
Vamidothion, XMC, Xylylcarb, Yl 5301 / 5302, Zetamethrin. O 00/03976Vamidothione, XMC, xylylcarb, Yl 5301/5302, zetamethrin. O 00/03976
- 62 -- 62 -
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstumsregulatoren ist möglich.A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.
Die erfindungsgemäßen Wirkstoffe können ferner beim Einsatz als Insektizide und Nematizide in ihren handelsüblichen Formulierungen sowie in den aus diesenWhen used as insecticides and nematicides, the active compounds according to the invention can also be used in their commercially available formulations and in the formulations thereof
Formulierungen bereiteten Anwendungsformen in Mischung mit Synergisten vorliegen. Synergisten sind Verbindungen, durch die die Wirkung der Wirkstoffe gesteigert wird, ohne daß der zugesetzte Synergist selbst aktiv wirksam sein muß.Formulations prepared use forms are available in a mixture with synergists. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoffkoiizentration der Anwendungsformen kann von 0,0000001 bis zu 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,0001 und 1 Gew.-% liegen.The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active ingredient concentration of the use forms can be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichenThe application takes place in a customary manner adapted to the application forms
Weise.Wise.
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnet sich der Wirkstoff durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekalkten Unterlagen aus.When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
In entsprechenden Aufwandmengen zeigen die erfindungsgemäßen Verbindungen auch herbizide Eigenschaften bzw. pflanzwachstumsregulierende Wirkung, wie z.B. einen Defoliant-Effekt.At appropriate application rates, the compounds according to the invention also show herbicidal properties or plant growth-regulating activity, such as a defoliant effect.
Die erfindungsgemäßen Wirkstoffe wirken nicht nur gegen Pflanzen-, Hygiene- und Vorratsschädlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ektoparasiten) wie Schildzecken, Lederzecken, Räudemilben, Laufmilben, Fliegen (stechend und leckend), parasitierende Fliegenlarven, Läuse. Haarlinge, Federlinge und Flöhe. Zu diesen Parasiten gehören: Aus der Ordnung der Anoplurida z.B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp..The active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae and lice. Hair lice, featherlings and fleas. These parasites include: From the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
Aus der Ordnung der Mallophagida und den Unterordnungen Amblycerina sowieFrom the order of the Mallophagida and the subordinates Amblycerina as well
Ischnocerina z.B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.. Aus der Ordnung Diptera und den Unterordnungen Nematocerina sowie Brachycerina z.B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp.,Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .. From the order Diptera and the subordinates Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp.,
Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp..Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp ., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
Aus der Ordnung der Siphonapterida z.B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp..From the order of the Siphonapterida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
Aus der Ordnung der Heteropterida z.B. Cimex spp., Triatoma spp., Rhodnius spp.,From the order of the Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp.,
Panstrongylus spp..Panstrongylus spp ..
Aus der Ordnung der Blattarida z.B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp..From the order of the Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp ..
Aus der Unterklasse der Acaria (Acarida) und den Ordnungen der Meta- sowie Mesostigmata z.B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.. Aus der Ordnung der Actinedida (Prostigmata) und Acaridida (Astigmata) z.B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp..From the subclass of Acaria (Acarida) and the orders of the Meta- and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp .. From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
Die erfindungsgemäßen Wirkstoffe der Formel (I) eignen sich auch zur Bekämpfung von Arthropoden, die landwirtschaftliche Nutztiere, wie z.B. Rinder, Schafe, Ziegen,The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats,
Pferde, Schweine, Esel, Kamele, Büffel, Kaninchen, Hühner, Puten, Enten, Gänse, Bienen, sonstige Haustiere wie z.B. Hunde, Katzen, Stubenvögel, Aquarienfische sowie sogenannte Versuchstiere, wie z.B. Hamster, Meerschweinchen, Ratten und Mäuse befallen. Durch die Bekämpfung dieser Arthropoden sollen Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig usw.) vermindert werden, so daß durch den Einsatz der erfindungsgemäßen Wirkstoffe eine wirtschaftlichere und einfachere Tierhaltung möglich ist.Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
Die Anwendung der erfindungsgemäßen Wirkstoffe geschieht im Veterinärsektor in bekannter Weise durch enterale Verabreichung in Form von beispielsweise Tabletten,The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets,
Kapseln, Tränken, Drenchen, Granulaten, Pasten, Boli, des feed-through-Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie zum Beispiel durch Injektionen (intramuskulär, subcutan, intravenös, intraperitonal u.a.), Implantate, durch nasale Applikation, durch dermale Anwendung in Form beispielsweise des Tauchens oder , Badens (Dippen), Sprühens (Spray), Aufgießens (Pour-on und Spot-on), desCapsules, watering, drenching, granules, pastes, boluses, the feed-through method, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal Application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), des
Waschens, des Einpuderns sowie mit Hilfe von wirkstoffhaltigen Formköφern, wie Halsbändern, Ohrmarken, Schwanzmarken, Gliedmaßenbändern, Halftern, Markierungsvorrichtungen usw. Bei der Anwendung für Vieh, Geflügel, Haustiere etc. kann man die Wirkstoffe der Formel (I) als Formulierungen (beispielsweise Pulver, Emulsionen, fließfähige Mittel), die die Wirkstoffe in einer Menge von 1 bis 80 Gew.-% enthalten, direkt oder nach 100 bis 10 000-facher Verdünnung anwenden oder sie als chemisches Bad verwenden.Washing, powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc. When used for cattle, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
Außerdem wurde gefunden, daß die erfindungsgemäßen Verbindungen der Formel (I) eine hohe insektizide Wirkung gegen Insekten zeigen, die technische Materialien zerstören.It has also been found that the compounds of the formula (I) according to the invention have a high insecticidal action against insects which destroy industrial materials.
Beispielhaft und vorzugsweise - ohne jedoch zu limitieren - seien die folgenden Insekten genannt:The following insects may be mentioned by way of example and preferably, but without limitation:
Käfer wieBeetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium caφini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis; Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutusHylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium caφini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesceses, Lyctus pubesculuses, Lyctus pubescuses, Lyctus pubescusis, Lyctus pubescusis, Lyctus linearesces rug Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus
Hautflügler wieSkin wings like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augurSirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur
Termiten wieTermites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus. Borstenschwänze, wie Lepisma saccarina.Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus. Bristle tails, such as Lepisma saccarina.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht-lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz und Holzverarbeitungsprodukte und Anstrichmittel.In the present context, technical materials are understood to mean non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints.
Ganz besonders bevorzugt handelt es sich bei dem vor Insektenbefall zu schützenden Material um Holz und Holzverarbeitungsprodukte.The material to be protected against insect infestation is very particularly preferably wood and wood processing products.
Unter Holz und Holzverarbeitungsprodukten, welche durch das erfindungsgemäßeAmong wood and wood processing products, which by the invention
Mittel bzw. dieses enthaltende Mischungen geschützt werden kann, ist beispielhaft zu verstehen: Bauholz, Holzbalken, Eisenbahnschwellen, Brückenteile, Bootsstege, Holzfahrzeuge, Kisten, Paletten, Container, Telefonmasten, Holzverkleidungen, Holzfenster und- türen, Sperrholz, Spanplatten, Tischlerarbeiten oder Holzprodukte, die ganz allgemein beim Hausbau oder in der Bautischlerei Verwendung finden.Agents or mixtures containing them can be protected is to be understood as examples: construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry work or wooden products, which are generally used in house construction or in carpentry.
Die Wirkstoffe können als solche, in Form von Konzentraten oder allgemein üblichen Formulierungen wie Pulver, Granulate, Lösungen, Suspensionen, Emulsionen oder Pasten angewendet werden.The active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
Die genannten Formulierungen können in an sich bekannter Weise hergestellt werden, z.B. durch Vermischen der Wirkstoffe mit mindestens einem Lösungs- bzw. Verdünnungsmittel, Emulgator, Dispergier- und/oder Binde- oder Fixiermittels, Wasser-Repellent, gegebenenfalls Sikkative und UV-Stabilisatoren und gegebenen- .falls Farbstoffen und Pigmenten sowie weiteren Verarbeitungshilfsmitteln.The formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and, if appropriate, dyes and pigments and further processing aids.
Die zum Schutz von Holz und Holzwerkstoffen verwendeten insektiziden Mittel oder Konzentrate enthalten den erfindungsgemäßen Wirkstoff in einer Konzentration von 0,0001 bis 95 Gew.-%, insbesondere 0,001 bis 60 Gew.-%. Die Menge der eingesetzten Mittel bzw. Konzentrate ist von der Art und dem Vorkommen der Insekten und von dem Medium abhängig. Die optimale Einsatzmenge kann bei der Anwendung jeweils durch Testreihen ermittelt werden. Im allgemeinen ist es jedoch ausreichend 0,0001 bis 20 Gew.-%, vorzugsweise 0,001 bis 10 Gew.-%, des Wirkstoffs, bezogen auf das zu schützende Material, einzusetzen.The insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight. The amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
Als Lösungs- und/oder Verdünnungsmittel dient ein organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder ein öliges oder ölartiges schwer flüchtiges organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder ein polares organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder Wasser und gegebenenfalls einen Emulgator und/oder Netzmittel.An organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
Als organisch-chemische Lösungsmittel werden vorzugsweise ölige oder ölartige Lösungsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, eingesetzt. Als derartige schwerflüchtige, wasserunlösliche, ölige und ölartige Lösungsmittel werden entsprechende Mineralöle oder deren Aromatenfraktionen oder mineralölhaltige Lösungsmittelgemische, vorzugsweise Testbenzin, Petroleum und/oder Alkylbenzol verwendet.The organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
Vorteilhaft gelangen Mineralöle mit einem Siedebereich von 170 bis 220°C, Testbenzin mit einem Siedebereich von 170 bis 220°C, Spindelöl mit einem Siedebereich von 250 bis 350°C, Petroleum bzw. Aromaten vom Siedebereich von 160 bis 280°C, Teφentinöl und dgl. zum Einsatz.Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, Teφentinöl and Like. Used.
In einer bevorzugten Ausführungsform werden flüssige aliphatische Kohlenwasserstoffe mit einem Siedebereich von 180 bis 210°C oder hochsiedende Gemische von aromatischen und aliphatischen Kohlenwasserstoffen mit einem Siedebereich von 180 bis 220°C und/oder Spindeöl und/oder Monochlomaphthalin, vorzugsweise α- Monochlornaphthalin, verwendet. O 00/03976In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochlomaphthalene, preferably α-monochloronaphthalene, are used. O 00/03976
- 68 -- 68 -
Die organischen schwerflüchtigen öligen oder ölartigen Lösungsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, können teilweise durch leicht oder mittelflüchtige organisch-chemische Lösungsmittel ersetzt werden, mit der Maßgabe, daß das Lösungsmittelgemisch ebenfalls eine Verdunstungszahl über 35 und einen Flammpunkt oberhalb 30°C, vorzugsweise oberhalb 45°C, aufweist und daß das Insektizid-Fungizid-Gemisch in diesem Lösungsmittelgemisch löslich oder emulgierbar ist.The organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
Nach einer bevorzugten Ausführungsform wird ein Teil des organisch-chemischen Lösungsmittel oder Lösungsmittelgemisches oder ein aliphatisches polares organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch ersetzt. Vorzugsweise gelangen Hydroxyl- und/oder Ester- und/oder Ethergruppen enthaltende aliphatische organisch-chemische Lösungsmittel wie beispielsweise Glycolether, Ester oder dgl. zur Anwendung.According to a preferred embodiment, part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced. Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
Als organisch-chemische Bindemittel werden im Rahmen der vorliegenden Erfindung die an sich bekannten wasserverdünnbaren und/oder in den eingesetzten organisch-chemischen Lösungsmitteln löslichen oder dispergier- bzw. emulgierbaren Kunstharze und/oder bindende trocknende Öle, insbesondere Bindemittel bestehend aus oder enthaltend ein Acrylatharz, ein Vinylharz, z.B. Polyvinylacetat, Polyesterharz, Polykondensations- oder Polyadditionsharz, Polyurethanharz, Alkydharz bzw. modifiziertes Alkydharz, Phenolharz, Kohlenwasserstoffharz wie Inden-Cumaron- harz, Siliconharz, trocknende pflanzliche und/oder trocknende Öle und/oder physikalisch trocknende Bindemittel auf der Basis eines Natur- und/oder Kunstharzes ver- wendet.In the context of the present invention, the known organic-chemical binders are the water-thinnable and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / / or synthetic resin.
Das als Bindemittel verwendete Kunstharz kann in Form einer Emulsion, Dispersion oder Lösung, eingesetzt werden. Als Bindemittel können auch Bitumen oder bituminöse Substanzen bis zu 10 Gew.-%, verwendet werden. Zusätzlich können an sich bekannte Farbstoffe, Pigmente, wasserabweisende Mittel, Geruchskorrigentien und Inhibitoren bzw. Korrosionsschutzmittel und dgl. eingesetzt werden.The synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, in itself Known dyes, pigments, water-repellent agents, odor correctors and inhibitors or anticorrosive agents and the like can be used.
Bevorzugt ist gemäß der Erfindung als organisch-chemische Bindemittel mindestens ein Alkydharz bzw. modifiziertes Alkydharz und/oder ein trocknendes pflanzlichesAccording to the invention, preference is given to at least one alkyd resin or modified alkyd resin and / or a drying plant-based organic-chemical binder
Öl im Mittel oder im Konzentrat enthalten. Bevorzugt werden gemäß der Erfindung Alkydharze mit einem Ölgehalt von mehr als 45 Gew.-%, vorzugsweise 50 bis 68 Gew.-%, verwendet.Contain oil in the medium or in the concentrate. Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
Das erwähnte Bindemittel kann ganz oder teilweise durch ein Fixierungs- mittel(gemisch) oder ein Weichrnacher(gemisch) ersetzt werden. Diese Zusätze sollen einer Verflüchtigung der Wirkstoffe sowie einer Kristallisation bzw. Ausfällen! vorbeugen. Vorzugsweise ersetzen sie 0,01 bis 30 % des Bindemittels (bezogen auf 100 % des eingesetzten Bindemittels).All or part of the binder mentioned can be replaced by a fixative (mixture) or a Weichrnacher (mixture). These additives are intended to volatilize the active ingredients and crystallize or precipitate! prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
Die Weichmacher stammen aus den chemischen Klassen der Phthalsäureester wie Dibutyl-, Dioctyl- oder Benzylbutylphthalat, Phosphorsäureester wie Tributyl- phosphat, Adipinsäureester wie Di-(2-ethylhexyl)-adipat, Stearate wie Butylstearat oder Amylstearat, Oleate wie Butyloleat, Glycerinether oder höhermolekulare Gly- kolether, Glycerinester sowie p-Toluolsulfonsäureester.The plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
Fixierungsmittel basieren chemisch auf Polyvinylalkylethern wie z.B. Polyvinyl- methylether oder Ketonen wie Benzophenon, Ethylenbenzophenon.Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
Als Lösungs- bzw. Verdünnungsmittel kommt insbesondere auch Wasser in Frage, gegebenenfalls in Mischung mit einem oder mehreren der oben genannten organischchemischen Lösungs- bzw. Verdünnungsmittel, Emulgatoren und Dispergatoren.Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
Ein besonders effektiver Holzschutz wird durch großtechnische Imprägnierverfahren, z.B. Vakuum, Doppel vakuum oder Druckverfahren, erzielt. Die anwendungsfertigen Mittel können gegebenenfalls noch weitere Insektizide und gegebenenfalls noch ein oder mehrere Fungizide enthalten.A particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes. The ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
Als zusätzliche Zumischpartner kommen vorzugsweise die in der Wo 94/29 268 genannten Insektizide und Fungizide in Frage. Die in diesem Dokument genannten Verbindungen sind ausdrücklicher Bestandteil der vorliegenden Anmeldung.The insecticides and fungicides mentioned in Wo 94/29 268 are particularly suitable as additional mixing partners. The compounds mentioned in this document are an integral part of the present application.
Ganz besonders bevorzugte Zumischpartner können Insektizide, wie Chlorpyriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin,Very particularly preferred mixing partners can be insecticides, such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin,
Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron und Triflumuron, sowie Fungizide wie Epoxyconazole, Hexaconazole, Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-Iod-2-propinyl-butylcarbamat, N-Octyl-isothiazolin-3-on und 4,5-Dichlor-N- octylisothiazolin-3-on, sein.Permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlofluanid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl -isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.
Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe gehen aus den nachfolgenden Beispielen hervor. The preparation and use of the active compounds according to the invention can be seen from the examples below.
HerstellungsbeispieleManufacturing examples
Beispiel 1example 1
Zu 7,8 g (0,05 Mol) [R]-4-Chlor-2-methylbenzylamin in 30 ml Methanol gibt man 5,0 g (0,05 Mol) N-Cyano-ethanimidsäuremethylester und läßt das Reaktionsgemisch 2 Stunden bei Raumtemperatur rühren. Anschließend wird mit Wasser versetzt, der ausgefallene Niederschlag abfiltriert und getrocknet.5.0 g (0.05 mol) of methyl N-cyanoethanimidate are added to 7.8 g (0.05 mol) of [R] -4-chloro-2-methylbenzylamine in 30 ml of methanol and the reaction mixture is left for 2 hours Stir room temperature. Then water is added, the precipitate which has separated out is filtered off and dried.
Man erhält 7,0 g (63% der Theorie) [R]-N-Cyano-N'-(4-chloφhenyl-eth-l-yl)-ethan- imidamid vom Schmelzpunkt 125°C und einem Drehwinkel [a] ^ = + 252,5° (CH3OH). This gives 7.0 g (63% of theory) of [R] -N-cyano-N '- (4-chloro-phenyl-eth-1-yl) -ethanimidamide with a melting point of 125 ° C. and an angle of rotation [a] ^ = + 252.5 ° (CH 3 OH).
O 00/03976O 00/03976
72 -72 -
Analog bzw. gemäß den allgemeinen Verfahrensangaben werden die folgenden erfindungsgemäßen Verbindungen erhalten:The following compounds according to the invention are obtained analogously or according to the general process instructions:
Tabelle ATable A
O 00/03976 O 00/03976
-73-73
Tabelle A (Fortsetzung)Table A (continued)
O 00/03976 O 00/03976
-74--74-
Tabelle A (Fortsetzung)Table A (continued)
O 00/03976 O 00/03976
- 75- 75
Tabelle A (Fortsetzung)Table A (continued)
Bsp.- Rl R2 R4 R5 R6 Physik. Konst.Example - R1 R2 R4 R5 R6 Physics. Const.
Nr.No.
Fp. 126°CMp 126 ° C
50 CH, H H C2H5 -Cl (S-Isomer)50 CH, HHC 2 H 5 -Cl (S-isomer)
51 CH, H H CH, Λ -OCH, Fp. 71°C (S-Isomer)51 CH, H H CH, Λ -OCH, mp. 71 ° C (S-isomer)
52 CH3 H H CH3 -CH2CH2- \J OCH, Fp. 87°C52 CH 3 HH CH 3 -CH 2 CH 2 - \ J OCH, mp 87 ° C
53 CH3 H H CH3 -CH2CH2- Λ /4-OCH, Fp. 75°C (R-Isomer)53 CH 3 HH CH 3 -CH 2 CH 2 - Λ / 4-OCH, mp. 75 ° C (R-isomer)
54 CH3 H H C2H5 -CH2OCH2- Öl54 CH 3 HHC 2 H 5 -CH 2 OCH 2 - oil
Cl =\ Cl = \
55 CH, H H C2H5 -CH2OCH2- Fp. 83°C55 CH, HHC 2 H 5 -CH 2 OCH 2 - mp 83 ° C
56 CH, H H C2H5 -CH2OCH2- Fp. 95°C 56 CH, HHC 2 H 5 -CH 2 OCH 2 - mp 95 ° C
57 CH3 H H C2H5 -CH2OCH2- Öl57 CH 3 HHC 2 H 5 -CH 2 OCH 2 - oil
^S^CI^ S ^ CI
58 CH3 H H C2H5 -CH2OCH2- Fp. 86°C58 CH 3 HHC 2 H 5 -CH 2 OCH 2 - mp 86 ° C
59 CH3 H H C2H5 -CFI2OCH2- Öl 59 CH 3 HHC 2 H 5 -CFI 2 OCH 2 - oil
60 CH3 H H C2H5 -CH2OCH2- Öl60 CH 3 HHC 2 H 5 -CH 2 OCH 2 - oil
61 CH3 H H C2H5 -CH2OCH2- Öl61 CH 3 HHC 2 H 5 -CH 2 OCH 2 - oil
ClCl
62 CH3 H H C2H5 -CH2OCH2- Öl62 CH 3 HHC 2 H 5 -CH 2 OCH 2 - oil
-Q-Cl -Q- Cl
63 CH3 H H C2H5 -CH2OCH2- Öl63 CH 3 HHC 2 H 5 -CH 2 OCH 2 - oil
%J% J
FX viskosFX viscous
64 CFI3 H H C2H5 -CH2OCH2- 3~ζ~}64 CFI 3 HHC 2 H 5 -CH 2 OCH 2 - 3 ~ ζ ~ }
65 CH, H H C2H5 -CH2OCH- Fp. 79°C 65 CH, HHC 2 H 5 -CH 2 OCH- mp 79 ° C
66 CH, H H H -CHoSCH^ λ -Cl viskos Tabelle A (Fortsetzung)66 CH, HHH -CHoSCH ^ λ -Cl viscous Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Bsp.- Rl R2 R4 R5 X R« Physik.Example - R1 R2 R4 R5 X R «Physics.
Nr. Konst.No.
96 CH3 H H H ~ -o Fp. 168°C96 CH 3 HHH ~ -o mp 168 ° C
97 CH3 H H H - Fp. 150°C c^ \ (97 CH 3 HHH - mp 150 ° C c ^ \ (
98 CH3 H H H - Fp. 159°C98 CH 3 HHH - mp 159 ° C
- "cι - "cι
99 CH3 H H H - Fp. 145°C99 CH 3 HHH - mp 145 ° C
\I J\ I J
100 CH3 H H H - Fp. 145°C100 CH 3 HHH - mp 145 ° C
\i J\ i J
101 CH3 H H H - Fp. 167°C101 CH 3 HHH - mp 167 ° C
102 CH3 CH3 H H - viskos 102 CH 3 CH 3 HH - viscous
103 CH3 H H H -103 CH 3 HHH -
CH, H H H Hfio Fp. 151°CCH, HHH Hfi or mp 151 ° C
104 CH, Fp. 113°C _104 CH, mp. 113 ° C _
105 CH, H H H F3CO Fp. 106°C105 CH, HHHF 3 CO mp 106 ° C
106 CH, H H H Fp. 114°C w r∞F*106 CH, HHH mp 114 ° C wr ∞F *
107 CH, H H H O2N Fp. 192°C >107 CH, HHHO 2 N mp 192 ° C>
108 CH, CH3 H H =<N°2 Fp. 124°C108 CH, CH 3 HH = < N ° 2 mp 124 ° C
109 CH, H H H H3CO Fp. 125°C109 CH, HHHH 3 CO mp 125 ° C
1 10 CH3 H H H OCH, Fp. 92°C1 10 CH 3 HHH OCH, mp 92 ° C
11 1 CH, H H H \\ -°CH^ Fp. 112°C Tabelle A (Fortsetzung)11 1 CH, HHH \\ - ° CH ^ mp 112 ° C Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
BsP " | Rl R2 R R5 R6 Physik. Bs P " | Rl R 2 R R5 R6 physics.
Nr. Konst.No.
139 CH3 H CH, H viskos139 CH 3 H CH, H viscous
-Ocι -O cι
140 CH, H CH3 H Fp. 131°C -£>cι (R-Isomer)140 CH, H CH 3 H mp 131 ° C - £> cι (R-isomer)
141 CH, H CH, H viskos (S-Isomer)141 CH, H CH, H viscous (S-isomer)
142 CH, H C2H5 H viskos 142 CH, HC 2 H 5 H viscous
142 CH, H C,H7-n H Fp. 86°C i fcl 142 CH, HC, H 7 -n H mp 86 ° C if cl
144 CH3 H CH, H Cl Fp. 156°C144 CH 3 H CH, H Cl mp 156 ° C
145 CH, H CH, H145 CH, H CH, H
146 CH, H CH3 H x Fp. 131°C146 CH, H CH 3 H x mp 131 ° C
Fp. >250°CMp> 250 ° C
147 CH, H CH, H CF, Fp. 105°C147 CH, H CH, H CF, mp 105 ° C
148 CH, H CH, H Fp. 1 15°C x_rF 148 CH, H CH, H Mp. 1 15 ° C x_r F
149 CH3 H CH3 H OO Fp. 110°C149 CH 3 H CH 3 H OO mp 110 ° C
150 CH, H CH, H H3CO =^ Fp. 135°C150 CH, H CH, HH 3 CO = ^ mp 135 ° C
OO
151 CH, H CH, H /==^OCH3 Fp. 140°C151 CH, H CH, H / == ^ OCH 3 mp 140 ° C
152 CH3 H CH3 H -CH2CH2- CF, Fp. 95°C152 CH 3 H CH 3 H -CH 2 CH 2 - CF, mp 95 ° C
153 CH3 H CH3 H -CH2CH2- viskos153 CH 3 H CH 3 H -CH 2 CH 2 - viscous
154 | CH3 H CH3 H -CH2CH- viskos Tabelle A (Fortsetzung)154 | CH 3 H CH 3 H -CH 2 CH viscous Table A (continued)
Bsp.- Rl R2 R R5 X R6 Physik.Example - Rl R2 R R5 X R6 Physics.
Nr. Konst.No.
155 CH3 H H H -CH(CH3)- Fp. 96°C155 CH 3 HHH -CH (CH 3 ) - mp 96 ° C
156 CH3 H CH3 H -CH(CH3)CH2- viskos 156 CH 3 H CH 3 H -CH (CH 3 ) CH 2 - viscous
157 CH3 H CH3 H -CH(CH3)CH2- -χ- viskos157 CH 3 H CH 3 H -CH (CH 3 ) CH 2 - -χ- viscous
158 CH3 H CH3 H -CH(CH3)CH2- 0~cι Fp. 108°C158 CH 3 H CH 3 H -CH (CH 3 ) CH 2 - ~ ~ mp 108 ° C
159 CH3 H CH3 H -CH(CH3)CH2- viskos159 CH 3 H CH 3 H -CH (CH 3 ) CH 2 - viscous
~ -F ~ - F
160 CH3 H CH3 H -CH(CH3)CH2- Fp. 122°C160 CH 3 H CH 3 H -CH (CH 3 ) CH 2 - mp 122 ° C
- -Br - - Br
161 CH3 H CH3 H -CH(CH3)CH2- viskos161 CH 3 H CH 3 H -CH (CH 3 ) CH 2 - viscous
162 CH3 H CH3 H -CH(CH3)CH2- Fp. 120°C162 CH 3 H CH 3 H -CH (CH 3 ) CH 2 - mp 120 ° C
163 CH3 H CH3 H *~ Fp. 134°C 163 CH 3 H CH 3 H * ~ mp 134 ° C
164 CH3 H CH3 H - α viskos164 CH 3 H CH 3 H - α viscous
165 CH3 H H H -C(CH3)=CH- Fp. 79°C165 CH 3 HHH -C (CH 3 ) = CH- mp 79 ° C
-Q-c-Q-c
166 CH3 H H H -C(CH3)2-166 CH 3 HHH -C (CH 3 ) 2 -
0~cι Fp. 169°C0 ~ cp mp 169 ° C
167 CH3 H CH3 H -CH2C(CH3)2- viskos167 CH 3 H CH 3 H -CH 2 C (CH 3 ) 2 - viscous
-Q-cι-Q-cι
168 CH3 H CH3 H ~ viskos168 CH 3 H CH 3 H ~ viscous
169 CH3 H C2H5 H -CH2- X169 CH 3 HC 2 H 5 H -CH 2 - X
2- -o viskos 2 - -o viscous
170 CH3 H CH3 H -CH2CH viskos170 CH 3 H CH 3 H -CH 2 CH viscous
171 CH3 H CH3 H -CH2- Fp. 84°C171 CH 3 H CH 3 H -CH 2 - mp 84 ° C
^ Tabelle A (Fortsetzung)^ Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Tabelle A (Fortsetzung) Table A (continued)
Bsp.- Rl R2 R4 R5 XExample - Rl R 2 R4 R5 X
Nr. ≠ Physik. Konst.No. ≠ Physics. Const.
318 C2H5 H H C2H5 -CH2CH2-318 C 2 H 5 HHC 2 H 5 -CH 2 CH 2 -
^\S^CH3 ^ \ S ^ CH 3
319 C3H7-n H H C2H5 -CH7CH2- 319 C 3 H 7 -n HHC 2 H 5 -CH 7 CH 2 -
320 C3H7-i H H C2H5 -CH2CH2- s cH3 320 C 3 H 7 -i HHC 2 H 5 -CH 2 CH 2 - s cH 3
Tabelle BTable B
AnvyendungsbeispieleApplication examples
Beispiel AExample A
Grenzkonzentration - TestLimit concentration test
Testnematode: Meloidogyne incognitaTest nematode: Meloidogyne incognita
Lösungsmittel: 4 Gewichtsteile AcetonSolvent: 4 parts by weight of acetone
Emulgator: 1 Gewichtsteil AlkylarylpolyglykoletherEmulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Die Wirkstoffzubereitung wird innig mit dem Boden vermischt, der mit den Test- nematoden verseucht ist. Dabei spielt die Konzentration des Wirkstoffes in der Zubereitung praktisch keine Rolle, entscheidend ist allein die Wirkstoffmenge pro Volumeneinheit Boden, welche in ppm (= mg/1) angegeben wird. Man füllt den be- handelten Boden in Töpfe, sät Salat ein und hält die Töpfe bei einer Gewächshaustemperatur von 25°C.The active ingredient preparation is mixed intimately with the soil that is contaminated with the test nematodes. The concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (= mg / 1). The treated soil is poured into pots, seeds are sown and the pots are kept at a greenhouse temperature of 25 ° C.
Nach drei Wochen werden die Salatwurzeln auf Nematodenbefall (Wurzelgallen) untersucht und der Wirkungsgrad des Wirkstoffes in % bestimmt. Der Wirkungsgrad ist 100%, wenn der Befall vollständig vermieden wird, er ist 0%, wenn der Befall genau so hoch ist wie bei den Kontrollpflanzen in unbehandeltem, aber in gleicher Weise verseuchtem Boden.After three weeks, the lettuce roots are examined for nematode infestation (root galls) and the efficiency of the active ingredient is determined in%. The efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is as high as that of the control plants in untreated, but equally contaminated soil.
Bei diesem Test bewirkt z.B. die Verbindung des Herstellungsbeispiels 1 bei einer beispielhaften Wirkstoffkonzentration von 20 ppm eine Abtötung von 100%. In this test e.g. the compound of preparation example 1 at an exemplary active ingredient concentration of 20 ppm, a kill of 100%.

Claims

O 00/03976 O 00/03976
- 97 -- 97 -
Patentansprücheclaims
1. Imidamid-Derivate der allgemeinen Formel (I),1. imidamide derivatives of the general formula (I),
in welcher in which
R für Cyano oder Nitro steht,R represents cyano or nitro,
R1 für Wasserstoff, gegebenenfalls substituiertes Alkyl, gegebenenfalls substituiertes Cycloalkyl oder gegebenenfalls substituiertes Phenyl steht,R 1 represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
R2 für Wasserstoff, gegebenenfalls substituiertes Alkyl oder gegebenen- falls substituiertes Cycloalkyl steht undR 2 represents hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl and
R3 für die GruppierungenR 3 for the groupings
R4 — C—χ-R6 ■ -Y-R7 und —O-R8 steht,R 4 - C — χ-R 6 ■ -YR 7 and —OR 8 ,
wobeiin which
R4 und R5 unabhängig voneinander für Wasserstoff, gegebenenfalls substituiertes Alkyl oder gegebenenfalls substituiertes Cycloalkyl stehen,R 4 and R 5 independently of one another represent hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl,
R6 und R7 unabhängig voneinander für gegebenenfalls substituiertes Aryl, jeweils gegebenenfalls substituiertes Cycloalkyl und Cycloalkenyi oder für einen gegebenenfalls substituierten mono-, bi- oder tricyclischen, Stickstoff-freien Heterocyclus stehen,R 6 and R 7 independently of one another for optionally substituted aryl, in each case optionally substituted cycloalkyl and Cycloalkenyi or represent an optionally substituted mono-, bi- or tricyclic, nitrogen-free heterocycle,
R8 für Alkyl oder gegebenenfalls substituiertes Aryl steht,R 8 represents alkyl or optionally substituted aryl,
X für eine Einfachbindung, für jeweils geradkettiges oder verzweigtes Alkandiyl, Alkendiyl, Alkindiyl sowie für die Gruppierungen -A-O-, -A-S-, -A-O-A'-, -A-S-A'-, -A-N(Alk)- oder -A-N(Alk)-A'- steht, wobei der Teil A an das C-Atom derX for a single bond, for in each case straight-chain or branched alkanediyl, alkenediyl, alkindiyl and for the groups -AO-, -AS-, -AO-A'-, -AS-A'-, -AN (Alk) - or -AN (Alk) -A'-, with part A attached to the carbon atom of
Gruppierung -C(R4R5)-X-R6 gebunden ist;Grouping -C (R 4 R 5 ) -XR 6 is bound;
Alk für Alkyl steht undAlk stands for alkyl and
A und A' unabhängig voneinander für geradkettiges oder verzweigtes Alkandiyl stehen undA and A 'independently of one another represent straight-chain or branched alkanediyl and
Y für eine Einfachbindung sowie die Gruppierungen -O-A-,Y for a single bond and the groupings -O-A-,
-O-A"-O-, -O-A"-S-, -O-A"-SO-, -O-A"-SO2-, -O-A"-O-A'- oder -O-A"-S-A'- steht, wobei das O-Atom dieser Gruppierung immer an dem N-Atom des Grundgerüsts der Formel (I) verknüpft ist;-OA "-O-, -OA" -S-, -OA "-SO-, -OA" -SO 2 -, -OA "-O-A'- or -OA"-S-A'-, the O atom of this group is always linked to the N atom of the basic structure of the formula (I);
A und A' die oben angegebene Bedeutung haben undA and A 'have the meaning given above and
A" für geradkettiges oder verzweigtes Alkandiyl mit mindestens 2 Kohlenstoffatomen zwischen den Heteroatomen steht.A "stands for straight-chain or branched alkanediyl having at least 2 carbon atoms between the heteroatoms.
r Maßgabe, daß für R = CN und R2 = H die Verbindungen, in welcher r Provided that for R = CN and R 2 = H the compounds in which
Ri = C2H5 und R = — ~ bzw.R i = C 2 H 5 and R = - ~ or
R1 = CH3 und R3 = — ~ bzw. ^^R 1 = CH 3 and R 3 = - ~ or ^^
Ri = i-C3H7 und R3 = _ ~Λ_CH R i = iC 3 H 7 and R 3 = _ ~ Λ_ CH
ausgenommen sind.with exception of.
Verfahren zur Herstellung der Imidamid-Derivate der allgemeinen Formel (I) gemäß Anspruch 1Process for the preparation of the imidamide derivatives of the general formula (I) according to Claim 1
dadurch gekennzeichnet, daß man Ethanimidsäureester der Formel (II)characterized in that ethanimidates of the formula (II)
R— N=C — Q— ZR - N = C - Q - Z
( II )(II)
in welcherin which
R und R1 die oben angegebene Bedeutung haben,R and R 1 have the meaning given above,
Q für Sauerstoff oder Schwefel steht undQ stands for oxygen or sulfur and
Z für Alkyl steht, mit Aminen der Formel (III)Z represents alkyl, with amines of the formula (III)
H-N — RJ l , ( HDHN - R J l, ( HD
in welcherin which
R2 und R3 die oben angegebene Bedeutung habenR 2 and R 3 have the meaning given above
in Gegenwart eines Verdünnungsmittels umsetzt.in the presence of a diluent.
3. Schädlingsbekämpfungsmittel, gekennzeichnet durch einen Gehalt an mindestens einem Imidamid-Derivat der Formel (I) gemäß Anspruch 1.3. pesticide, characterized by a content of at least one imidamide derivative of the formula (I) according to claim 1.
4. Verwendung von Imidamid-Derivaten der Formel (I) gemäß Anspruch 1 zur Bekämpfung von Schädlingen.4. Use of imidamide derivatives of the formula (I) according to Claim 1 for combating pests.
5. Verfahren zur Bekämpfung von Schädlingen, dadurch gekennzeichnet, daß man Imidamid-Derivate der Formel (I) gemäß Anspruch 1 auf Schädlinge und/oder ihren Lebensraum einwirken läßt.5. A method for controlling pests, characterized in that imidamide derivatives of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat.
6. Verfahren zur Herstellung von Schädlingsbekämpfungsmitteln, dadurch gekennzeichnet, daß man Imidamid-Derivate der Formel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Mitteln vermischt.6. A process for the preparation of pesticides, characterized in that imidamide derivatives of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active agents.
7. Verwendung von Imidamid-Derivaten der Formel (I) gemäß Anspruch 1 zur7. Use of imidamide derivatives of the formula (I) according to Claim 1 for
Herstellung von Schädlingsbekämpfungsmitteln. Manufacture of pesticides.
EP99936489A 1998-07-18 1999-07-07 Imidamide derivatives Expired - Lifetime EP1097128B1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19832447 1998-07-18
DE19832447 1998-07-18
DE19924273A DE19924273A1 (en) 1998-07-18 1999-05-27 New nitro- or cyano-imideamide derivatives, used as insecticides, acaricides, ectoparasiticides or especially nematocides
DE19924273 1999-05-27
PCT/EP1999/004747 WO2000003976A1 (en) 1998-07-18 1999-07-07 Imidamide derivatives

Publications (2)

Publication Number Publication Date
EP1097128A1 true EP1097128A1 (en) 2001-05-09
EP1097128B1 EP1097128B1 (en) 2004-05-12

Family

ID=26047539

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99936489A Expired - Lifetime EP1097128B1 (en) 1998-07-18 1999-07-07 Imidamide derivatives

Country Status (12)

Country Link
US (1) US6638979B1 (en)
EP (1) EP1097128B1 (en)
JP (1) JP2002520385A (en)
CN (1) CN1314881A (en)
AR (1) AR029738A1 (en)
AT (1) ATE266631T1 (en)
AU (1) AU5157399A (en)
BR (1) BR9912242A (en)
CA (1) CA2337773A1 (en)
EG (1) EG22587A (en)
ES (1) ES2221407T3 (en)
WO (1) WO2000003976A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19919790A1 (en) * 1999-04-30 2000-11-02 Bayer Ag Use of N-substituted heterocyclyalkylamines as herbicides and new N-substituted thienylaklylamines
DE10004084A1 (en) * 2000-01-31 2001-08-02 Bayer Ag Substituted imide derivatives
DE10221121A1 (en) * 2002-05-13 2003-12-04 Bayer Cropscience Ag N'-Cyano-N-methyl-imidamide derivatives
US9951097B2 (en) 2012-12-04 2018-04-24 The Board Of Trustees Of The University Of Illinois Antibacterial compounds targeting isoprenoid biosynthesis

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL84809A (en) 1987-11-06 1992-12-01 Ciba Geigy Process for the synthesis of 1-substituted imidazole- 5-carboxylic acids and derivatives thereof
SG52330A1 (en) 1989-06-14 1998-09-28 Smithkline Beecham Corp Imidazolyl-alkenoic acids
HU214992B (en) 1989-10-06 1998-12-28 Nippon Soda Co. Ltd. Process for producing amine derivatives and insecticide compositions containing them
JPH05310650A (en) 1991-08-22 1993-11-22 Nippon Soda Co Ltd New amine derivative its production and insecticide
DE19548783A1 (en) 1995-12-27 1997-07-03 Basf Ag Cyanimino oxime ethers, processes and intermediates for their preparation and their use in combating harmful fungi and animal pests
JPH09194451A (en) * 1996-01-22 1997-07-29 Nippon Soda Co Ltd Production of cyanoamidines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0003976A1 *

Also Published As

Publication number Publication date
ES2221407T3 (en) 2004-12-16
CN1314881A (en) 2001-09-26
BR9912242A (en) 2001-04-10
CA2337773A1 (en) 2000-01-27
EG22587A (en) 2003-04-30
AU5157399A (en) 2000-02-07
US6638979B1 (en) 2003-10-28
ATE266631T1 (en) 2004-05-15
AR029738A1 (en) 2003-07-16
JP2002520385A (en) 2002-07-09
WO2000003976A1 (en) 2000-01-27
EP1097128B1 (en) 2004-05-12

Similar Documents

Publication Publication Date Title
EP0880505A1 (en) Acylated 4-amino- and 4-hydrazinopyrimidines and their use as pesticides
EP0877741B1 (en) Acylated 5-amino-1,2,4-thiadiazoles as pesticides and fungicides
EP1084111A1 (en) Substituted 3-thiocarbamoylpyrazoles
DE19800400A1 (en) Substituted guanidine derivatives
EP1097128B1 (en) Imidamide derivatives
US7365098B2 (en) N&#39;-cyano-N-methyl-imidamide derivatives
EP1144407B1 (en) Cyclic guanidine derivatives and their use as pesticides
DE19924273A1 (en) New nitro- or cyano-imideamide derivatives, used as insecticides, acaricides, ectoparasiticides or especially nematocides
EP1005461A1 (en) Acylated 5-aminoisothiazoles as pesticides and fungicides
EP0944608B1 (en) 4-cyclohexylphenyl-oxazolines and their use for controlling animal pests
EP0906016A1 (en) Use of pyrrolopyrimidines to combat pests
DE19629463A1 (en) New well tolerated glyoxylic acid thioamide derivatives
EP0973751A1 (en) Phenyl-amino-sulfonyl-urea derivatives as fungicides and pesticides
DE19629466A1 (en) New alkyl glyoxylic acid oxime derivatives to control pests,
EP1037877A1 (en) Acylated 4-aminopyridines as pesticides and fungicides
MXPA01000618A (en) Imidamide derivatives
DE19750401A1 (en) New pesticidal and fungicidal bicyclic 4-aminopyridine derivatives

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20010219

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

17Q First examination report despatched

Effective date: 20020919

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BAYER CROPSCIENCE AG

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040512

Ref country code: IE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040512

Ref country code: GB

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040512

Ref country code: FR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040512

Ref country code: FI

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040512

Ref country code: CY

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040512

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

Free format text: NOT ENGLISH

REG Reference to a national code

Ref country code: CH

Ref legal event code: EP

REG Reference to a national code

Ref country code: CH

Ref legal event code: NV

Representative=s name: E. BLUM & CO. PATENTANWAELTE

REG Reference to a national code

Ref country code: IE

Ref legal event code: FG4D

Free format text: GERMAN

REF Corresponds to:

Ref document number: 59909479

Country of ref document: DE

Date of ref document: 20040617

Kind code of ref document: P

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040707

Ref country code: AT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040707

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: MC

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040731

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20040731

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040812

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040812

Ref country code: DK

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 20040812

NLV1 Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act
GBV Gb: ep patent (uk) treated as always having been void in accordance with gb section 77(7)/1977 [no translation filed]

Effective date: 20040512

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2221407

Country of ref document: ES

Kind code of ref document: T3

REG Reference to a national code

Ref country code: IE

Ref legal event code: FD4D

BERE Be: lapsed

Owner name: BAYER CROPSCIENCE A.G.

Effective date: 20040731

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20050215

EN Fr: translation not filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20060628

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20060630

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20060704

Year of fee payment: 8

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: IT

Payment date: 20060731

Year of fee payment: 8

REG Reference to a national code

Ref country code: CH

Ref legal event code: PFA

Owner name: BAYER CROPSCIENCE AG

Free format text: BAYER CROPSCIENCE AG#ALFRED-NOBEL-STRASSE 50#40789 MONHEIM (DE) -TRANSFER TO- BAYER CROPSCIENCE AG#ALFRED-NOBEL-STRASSE 50#40789 MONHEIM (DE)

BERE Be: lapsed

Owner name: *BAYER CROPSCIENCE A.G.

Effective date: 20040731

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: PT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20041012

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070731

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20080201

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070731

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20070709

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070709

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20070707